関: dihydroergocryptine mesylate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/01 23:05:35」(JST)

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Dihydroergocryptine (DHEC, trade names Almirid, Cripar) is a dopamine agonist of the ergoline chemical class that is used as an antiparkinson agent.^[1] Dihydroergocryptine has been shown to be particularly effective as monotherapy in the early stages of Parkinson's disease. Initial monotherapy with a dopamine agonist (other examples include pergolide, pramipexole, and ropinirole) is associated with reduced risk for motor complications in Parkinson patients relative to levodopa.^[2] DHEC, like other dopamine agonists, aims to mimic the endogenous neurotransmitter and exert an antiparkinsonian effect.^[3] Recent evidence also supports that dopamine receptor agonists, instead of L-DOPA may slow or prevent the progression of Parkinson's disease.^[4]

Dihydroergocryptine can also be used in migraine prophylaxis,^[5] as well as for the treatment of low blood pressure in elderly patients and peripheral vascular disorder.^[6] More commonly, it is used in combination with two similar compounds, dihydroergocornine and dihydroergocristine. This mixture is called ergoloid or codergocrine.^[7]

Chemistry

Dihydroergocryptine is a mixture of two very similar compounds, alpha- and beta-dihydroergocryptine (epicriptine) at a ratio of 2:1.^[6] The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis of the parent compound ergocryptine, in which the proteinogenic amino acid leucine is replaced by isoleucine.^[8]

Dihydroergocryptine is a hydrogenated ergot derivative that is also structurally very similar to bromocriptine, another drug that has anti-Parkinson effects. DHEC differs in that it is hydrogenated in C9–C10 and lacks bromine in C2. In fact, all ergot derivatives are uniquely or mainly D₂-like receptor agonists.^[9]

Pharmacodynamics

Several in vitro and in vivo studies have demonstrated that dihydroergocriptine is an effective anti-Parkinson drug, most likely exerting its effects as a potent agonist of D₂ receptors. The K_d of DHEC is found to be around 5-8 nM at D2 receptors. Less certain is the contribution of its partial D₁ receptor and D₃ receptor agonist activity. DHEC has a lower affinity for D₁ and D₃ receptors (K_d is around 30 nM for both) than for D₂ receptors.^[3] It is widely believed that dopamine receptor agonists demonstrate their antiparkinsonian effects by stimulating D2 receptors primarily, but other dopamine receptors, such as D1 and D3 may be involved.^[3]

Remarkably, DHEC does not significantly interact with serotonergic and adrenergic receptors.^[9]

Pharmacokinetics

Dihydroergocriptine has two main pharmacokinetic advantages over levodopa.

The first pharmacokinetic advantage is its half-life of 12 to 16 hours. This relatively long half-life is considered to contribute to the compound's effectiveness in Parkinson's disease, particularly since it allows for more continuous stimulation of brain dopaminergic receptors than short-acting drugs such as levodopa. Though the exact reason is not known, continuous stimulation is considered to reduce risk for motor complications.^[2]

The second pharamcokinetic advantage is the lack of dietary influence on drug absorption. This characteristic also allows for more sustained dopamine receptor stimulation.^[9]

DHEC can be taken with a single oral dose and is rapidly absorbed. Peak plasma concentrations occur between 30 and 120 minutes after administration. The strong first-pass hepatic metabolism results in poor bioavailability. Less than 5% of the original dosage reaches the circulation.^[9]

Treatment

The relatively long half-life and lack of dietary influence of dihydroergocriptine is considered to contribute to the compound's effectiveness in Parkinson's disease, particularly since it allows for more continuous stimulation of brain dopaminergic receptors than short-acting drugs such as levodopa.^[9] DHEC is also proven to be a safe and effective in improving symptoms in Parkinson's patients.^[10]

Motor improvements

Motor improvements in Parkinson's patients are usually observed in patients who take at least a mean daily dose of approximately 40 mg.^[11] Patients on DHEC demonstrate a better score than if they were on L-Dopa on the Webster scale, a standardized rating scale of Parkinson's Disease symptoms such as gait parameters and dyskinesia.^[9]^[12] Another clinical study has shown that DHEC had superior efficacy in reducing the clinical and motorcomplications associated with long-term L-Dopa use, as well as in reducing the incidence and severity of adverse effects.^[13]

Neuroprotective effects

Activation of presynaptic dopamine autoreceptors by dihydroergocriptine leads to reduced dopamine receptor turnover and indirect antioxidant effects. In particular, further activation of intracellular kinase systems due to dopamine agonists are hypothesized to lead to antiapoptotic effects that also help in halting and slowing the disease progression.^[2] This may also contribute to prevention of development of motor fluctuations, though more research is needed.^[14]

Modern agonists like dihydroergocryptine typically cost two to three times more than levadopa therapy. More health economics assessments may be needed to determine whether the initial increased costs of the agonists are offset by less patients needing surgery in later stages of the disease.^[15]

Side effects

Dihydroergocryptine has been suggested to produce fewer side-effects and have similar efficacy to a classical dopamine agonist due to its biochemical profile.^[9] There is also no interference with levodopa metabolism.^[15] Although DHEC may come with some acute side-effects described further below, DHEC has overall good tolerability with little to no withdrawal or changes in its scheduling.^[16]

Acute side-effects usually accompany the beginning of treatment but tend to decrease as the patient develops increased tolerance to the drug.^[17] In randomized, double-blinded trials, individuals on different dopamine agonists, including dihydroergocryptine, did not differ in discontinuation rate associated with adverse events.^[18]^[19] However, there do seem to be a higher incidence of dopaminergic related side-effects such as hallucinations and gastrointestinal complaints tend to be more frequent.^[10]

Nausea
Vomiting
Anxiety
Cardiac arrhythmias
Postural hypotension
Somnolence
Hallucinations
Impulse control disorders
Peripheral oedema

References

^ Battistin, L.; Bardin, P. G.; Ferro-Milone, F.; Ravenna, C.; Toso, V.; Reboldi, G. (1999). "Alpha-dihydroergocryptine in Parkinson's disease: A multicentre randomized double blind parallel group study". Acta neurologica Scandinavica. 99 (1): 36–42. doi:10.1111/j.1600-0404.1999.tb00655.x. PMID 9925236.
^ ^a ^b ^c Antonini, A; Tolosa, E; Mizuno, Y; Yamamoto, M; Poewe, WH (October 2009). "A reassessment of risks and benefits of dopamine agonists in Parkinson's disease". Lancet neurology. 8 (10): 929–37. doi:10.1016/S1474-4422(09)70225-X. PMID 19709931.
^ ^a ^b ^c Gerlach, M; Double, K; Arzberger, T; Leblhuber, F; Tatschner, T; Riederer, P (October 2003). "Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.". Journal of neural transmission (Vienna, Austria : 1996). 110 (10): 1119–27. doi:10.1007/s00702-003-0027-5. PMID 14523624.
^ Parkinson Study, Group (Apr 3, 2002). "Dopamine transporter brain imaging to assess the effects of pramipexole vs levodopa on Parkinson disease progression". JAMA: the Journal of the American Medical Association. 287 (13): 1653–61. doi:10.1001/jama.287.13.1653. PMID 11926889.
^ Micieli, G.; Cavallini, A.; Marcheselli, S.; Mailland, F.; Ambrosoli, L.; Nappi, G. (2001). "Alpha-dihydroergocryptine and predictive factors in migraine prophylaxis". International journal of clinical pharmacology and therapeutics. 39 (4): 144–151. doi:10.5414/cpp39144. PMID 11332869.
^ ^a ^b Haberfeld, H, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-183-8.
^ Drugs.com: Ergoloid Mesylates
^ Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.
^ ^a ^b ^c ^d ^e ^f ^g Albanese, A; Colosimo, C (May 2003). "Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists". Acta neurologica Scandinavica. 107 (5): 349–55. doi:10.1034/j.1600-0404.2003.02049.x. PMID 12713527.
^ ^a ^b Bergamasco, B; Frattola, L; Muratorio, A; Piccoli, F; Mailland, F; Parnetti, L (June 2000). "Alpha-dihydroergocryptine in the treatment of de novo parkinsonian patients: results of a multicentre, randomized, double-blind, placebo-controlled study.". Acta neurologica Scandinavica. 101 (6): 372–80. doi:10.1034/j.1600-0404.2000.90295a.x. PMID 10877152.
^ Martignoni, E; Pacchetti, C; Sibilla, L; Bruggi, P; Pedevilla, M; Nappi, G (February 1991). "Dihydroergocryptine in the treatment of Parkinson's disease: a six months' double-blind clinical trial". Clin Neuropharmacol. 14 (1): 78–83. doi:10.1097/00002826-199102000-00006. PMID 1903079.
^ Ramaker, C; Marinus, J; Stiggelbout, AM; Van Hilten, BJ (September 2002). "Systematic evaluation of rating scales for impairment and disability in Parkinson's disease.". Movement disorders : official journal of the Movement Disorder Society. 17 (5): 867–76. doi:10.1002/mds.10248. PMID 12360535.
^ Battistin, L; Bardin, PG; Ferro-Milone, F; Ravenna, C; Toso, V; Reboldi, G (January 1999). "Alpha-dihydroergocryptine in Parkinson's disease: a multicentre randomized double blind parallel group study.". Acta neurologica Scandinavica. 99 (1): 36–42. doi:10.1111/j.1600-0404.1999.tb00655.x. PMID 9925236.
^ Olanow, CW (February 1992). "A rationale for dopamine agonists as primary therapy for Parkinson's disease". The Canadian journal of neurological sciences. Le journal canadien des sciences neurologiques. 19 (1 Suppl): 108–12. PMID 1349262.
^ ^a ^b Clarke, C.E.; Gutman, M. (30 November 2002). "Dopamine agonist monotherapy in Parkinson's Disease". Lancet. 360 (9347): 1767–1769. doi:10.1016/S0140-6736(02)11668-0. PMID 12480442.
^ Martignoni, E; Pacchetti, C; Sibilla, L; Bruggi, P; Pedevilla, M; Nappi, G (February 1991). "Dihydroergocryptine in the treatment of Parkinson's disease: a six months' double-blind clinical trial.". Clinical neuropharmacology. 14 (1): 78–83. doi:10.1097/00002826-199102000-00006. PMID 1903079.
^ Yamamoto, M; Schapira, AH (April 2008). "Dopamine agonists in Parkinson's disease". Expert Review of Neurotherapeutics. 8 (4): 671–7. doi:10.1586/14737175.8.4.671. PMID 18416667.
^ Rascol, O; Goetz, C; Koller, W; Poewe, W; Sampaio, C (May 4, 2002). "Treatment interventions for Parkinson's disease: an evidence based assessment". Lancet. 359 (9317): 1589–98. doi:10.1016/S0140-6736(02)08520-3. PMID 12047983.
^ Goetz, CG; Poewe, W; Rascol, O; Sampaio, C (May 2005). "Evidence-based medical review update: pharmacological and surgical treatments of Parkinson's disease: 2001 to 2004". Movement disorders : official journal of the Movement Disorder Society. 20 (5): 523–39. doi:10.1002/mds.20464. PMID 15818599.

English Journal

[Clinical comparision of alpha dihydroergocryptine against cabergoline in the treatment of the fibrocystic mastopathy].

Castillo-Huerta E1, Garibay-Valencia M, Mirabent-González F.Author information 1Hospital General Dr. Miguel Silva, Morelia, Michoacán.AbstractBACKGROUND: Fibrocystic breast disease is one of the most frequent conditions of the breast among women from 30 to 49 years, with a frequency of about 60%, hence the interest in studying and treating it with the most advanced and effective resources.
Ginecología y obstetricia de México.Ginecol Obstet Mex.2013 Jul;81(7):370-6.
BACKGROUND: Fibrocystic breast disease is one of the most frequent conditions of the breast among women from 30 to 49 years, with a frequency of about 60%, hence the interest in studying and treating it with the most advanced and effective resources.OBJECTIVE: To compare the efficacy and adverse eve
PMID 23971383

[Prescription of ergot derivatives for lactation inhibition in France: Current practices].

Mirkou A1, Suchovsky D, Gouraud A, Gillet A, Bernard N, Descotes J, Vial T.Author information 1Centre antipoison - centre de pharmacovigilance, hospices civils de Lyon, 162, avenue Lacassagne, 69003 Lyon, France.AbstractOBJECTIVES: To provide an overview of ergot derivatives prescription for lactation inhibition in France, either label (bromocriptine 2.5mg and lisuride 0.2mg) or off-label prescription (dihydroergocryptine and cabergoline).
Journal de gynécologie, obstétrique et biologie de la reproduction.J Gynecol Obstet Biol Reprod (Paris).2012 Apr;41(2):167-73. doi: 10.1016/j.jgyn.2011.06.002. Epub 2011 Oct 14.
OBJECTIVES: To provide an overview of ergot derivatives prescription for lactation inhibition in France, either label (bromocriptine 2.5mg and lisuride 0.2mg) or off-label prescription (dihydroergocryptine and cabergoline).PATIENTS AND METHODS: Analysis based on a questionnaire sent to all 618 Fren
PMID 22000685

The history of ergot of rye (Claviceps purpurea) III: 1940-80.

Lee MR.Author information University of Edinburgh, Edinburgh, UK.AbstractThe period 1940-80 in the history of ergot was dominated by two investigators, Arthur Stoll and Albert Hofmann. There was great excitement when their group isolated from ergot preparations the powerful psychotropic agent lysergic acid diethylamide (LSD). It was thought that this substance would help to find the cause of schizophrenia and other psychotic disorders, but it would prove to be a great disappointment and Hofmann would say later, in private, that he regretted having spent so much time on the compound. By contrast, bromocriptine, derived from ergocriptine, would prove a pivotal substance in our knowledge of dopamine receptors in the central nervous system. It is widely used for the suppression of lactation, the treatment of prolactinomas and the management of Parkinson's disease.
The journal of the Royal College of Physicians of Edinburgh.J R Coll Physicians Edinb.2010 Mar;40(1):77-80.
The period 1940-80 in the history of ergot was dominated by two investigators, Arthur Stoll and Albert Hofmann. There was great excitement when their group isolated from ergot preparations the powerful psychotropic agent lysergic acid diethylamide (LSD). It was thought that this substance would help
PMID 20503690

Japanese Journal

Determination of dihydroergocryptine in human plasma and urine samples using on-line sample extraction-column-switching reversed-phase liquid chromatography-mass spectrometry

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 808(2), 131-139, 2004-09-05
NAID 10016554458

ヒト腎組織内カテコールアミン受容体の検討

日本腎臓学会誌 28(8), 1145-1149, 1986
NAID 130004169244

メシル酸ジヒドロエルゴトキシンの抗血小板作用

血液と脈管 16(4), 374-379, 1985
NAID 130004261076

Related Pictures

★リンクテーブル★

リンク元	「ジヒドロエルゴクリプチン」
拡張検索	「dihydroergocryptine mesylate」

「ジヒドロエルゴクリプチン」

Dihydroergocryptine
Clinical data
Trade names	Almirid, Cripar
Pregnancy; category	Contraindicated;
Routes of; administration	Oral
ATC code	N04BC03 (WHO) (alpha/beta)
Legal status
Legal status	℞ (Prescription only);
Pharmacokinetic data
Biological half-life	12–16 hours
Identifiers
	IUPAC name (2R,4R,7R)-N- [(1S,2S,4R,7S)- 2-hydroxy- 7-(2-methylpropyl)- 5,8-dioxo- 4-(propan-2-yl)- 3-oxa- 6,9-diazatricyclo [7.3.0.02,6]dodecan-4-yl]- 6-methyl- 6,11-diazatetracyclo [7.6.1.02,7.012,16] hexadeca- 1(16),9,12,14-tetraene- 4-carboxamide;
Synonyms	12'-Hydroxy- 2'-(1-methylethyl)- 5'α-(2-methylpropyl)- 9,10α-dihydroergotaman- 3',6',18-trione;; OR; (5'α,10α)-9,10-dihydro- 12'-hydroxy-2'- (1-methylethyl)- 5'-(2-methylpropyl)- ergotaman- 3',6',18-trione
CAS Number	25447-66-9
PubChem (CID)	114948
ChemSpider	102887
UNII	67V3FSL2GL
ChEBI	CHEBI:59919
ChEMBL	CHEMBL1743263
ECHA InfoCard	100.042.706
Chemical and physical data
Formula	C32H43N5O5
Molar mass	577.715 g/mol
3D model (Jmol)	Interactive image
	SMILES O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3CC(C)C)(NC(=O)[C@@H]6C[C@@H]7c4cccc5c4c(cn5)C[C@H]7N(C)C6)C(C)C ;
	InChI InChI=1S/C32H43N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1 ; Key:PBUNVLRHZGSROC-VTIMJTGVSA-N ;
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英: dihydroergocryptine
関: メシル酸ジヒドロエルゴクリプチン

「dihydroergocryptine mesylate」

　　[★]

メシル酸ジヒドロエルゴクリプチン

関: dihydroergocryptine

[1] Battistin, L.; Bardin, P. G.; Ferro-Milone, F.; Ravenna, C.; Toso, V.; Reboldi, G. (1999). "Alpha-dihydroergocryptine in Parkinson's disease: A multicentre randomized double blind parallel group study". Acta neurologica Scandinavica. 99 (1): 36–42. doi:10.1111/j.1600-0404.1999.tb00655.x. PMID 9925236.

[Antonini2009-2] Antonini, A; Tolosa, E; Mizuno, Y; Yamamoto, M; Poewe, WH (October 2009). "A reassessment of risks and benefits of dopamine agonists in Parkinson's disease". Lancet neurology. 8 (10): 929–37. doi:10.1016/S1474-4422(09)70225-X. PMID 19709931.

[Gerlach_1119.E2.80.9327-3] Gerlach, M; Double, K; Arzberger, T; Leblhuber, F; Tatschner, T; Riederer, P (October 2003). "Dopamine receptor agonists in current clinical use: comparative dopamine receptor binding profiles defined in the human striatum.". Journal of neural transmission (Vienna, Austria : 1996). 110 (10): 1119–27. doi:10.1007/s00702-003-0027-5. PMID 14523624.

[4] Parkinson Study, Group (Apr 3, 2002). "Dopamine transporter brain imaging to assess the effects of pramipexole vs levodopa on Parkinson disease progression". JAMA: the Journal of the American Medical Association. 287 (13): 1653–61. doi:10.1001/jama.287.13.1653. PMID 11926889.

[5] Micieli, G.; Cavallini, A.; Marcheselli, S.; Mailland, F.; Ambrosoli, L.; Nappi, G. (2001). "Alpha-dihydroergocryptine and predictive factors in migraine prophylaxis". International journal of clinical pharmacology and therapeutics. 39 (4): 144–151. doi:10.5414/cpp39144. PMID 11332869.

[AustriaCodex-6] Haberfeld, H, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-183-8.

[7] Drugs.com: Ergoloid Mesylates

[8] Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.

[Albanese2003-9] ^ ^a ^b ^c ^d ^e ^f ^g Albanese, A; Colosimo, C (May 2003). "Dihydroergocriptine in Parkinson's disease: clinical efficacy and comparison with other dopamine agonists". Acta neurologica Scandinavica. 107 (5): 349–55. doi:10.1034/j.1600-0404.2003.02049.x. PMID 12713527.

[Bergamasco_372.E2.80.9380-10] Bergamasco, B; Frattola, L; Muratorio, A; Piccoli, F; Mailland, F; Parnetti, L (June 2000). "Alpha-dihydroergocryptine in the treatment of de novo parkinsonian patients: results of a multicentre, randomized, double-blind, placebo-controlled study.". Acta neurologica Scandinavica. 101 (6): 372–80. doi:10.1034/j.1600-0404.2000.90295a.x. PMID 10877152.

[11] Martignoni, E; Pacchetti, C; Sibilla, L; Bruggi, P; Pedevilla, M; Nappi, G (February 1991). "Dihydroergocryptine in the treatment of Parkinson's disease: a six months' double-blind clinical trial". Clin Neuropharmacol. 14 (1): 78–83. doi:10.1097/00002826-199102000-00006. PMID 1903079.

[12] Ramaker, C; Marinus, J; Stiggelbout, AM; Van Hilten, BJ (September 2002). "Systematic evaluation of rating scales for impairment and disability in Parkinson's disease.". Movement disorders : official journal of the Movement Disorder Society. 17 (5): 867–76. doi:10.1002/mds.10248. PMID 12360535.

[13] Battistin, L; Bardin, PG; Ferro-Milone, F; Ravenna, C; Toso, V; Reboldi, G (January 1999). "Alpha-dihydroergocryptine in Parkinson's disease: a multicentre randomized double blind parallel group study.". Acta neurologica Scandinavica. 99 (1): 36–42. doi:10.1111/j.1600-0404.1999.tb00655.x. PMID 9925236.

[14] Olanow, CW (February 1992). "A rationale for dopamine agonists as primary therapy for Parkinson's disease". The Canadian journal of neurological sciences. Le journal canadien des sciences neurologiques. 19 (1 Suppl): 108–12. PMID 1349262.

[Clarke_2002_1767.E2.80.931769-15] Clarke, C.E.; Gutman, M. (30 November 2002). "Dopamine agonist monotherapy in Parkinson's Disease". Lancet. 360 (9347): 1767–1769. doi:10.1016/S0140-6736(02)11668-0. PMID 12480442.

[16] Martignoni, E; Pacchetti, C; Sibilla, L; Bruggi, P; Pedevilla, M; Nappi, G (February 1991). "Dihydroergocryptine in the treatment of Parkinson's disease: a six months' double-blind clinical trial.". Clinical neuropharmacology. 14 (1): 78–83. doi:10.1097/00002826-199102000-00006. PMID 1903079.

[17] Yamamoto, M; Schapira, AH (April 2008). "Dopamine agonists in Parkinson's disease". Expert Review of Neurotherapeutics. 8 (4): 671–7. doi:10.1586/14737175.8.4.671. PMID 18416667.

[18] Rascol, O; Goetz, C; Koller, W; Poewe, W; Sampaio, C (May 4, 2002). "Treatment interventions for Parkinson's disease: an evidence based assessment". Lancet. 359 (9317): 1589–98. doi:10.1016/S0140-6736(02)08520-3. PMID 12047983.

[19] Goetz, CG; Poewe, W; Rascol, O; Sampaio, C (May 2005). "Evidence-based medical review update: pharmacological and surgical treatments of Parkinson's disease: 2001 to 2004". Movement disorders : official journal of the Movement Disorder Society. 20 (5): 523–39. doi:10.1002/mds.20464. PMID 15818599.

v t e GABA_A receptor positive allosteric modulators

Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (drinking alcohol) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol

Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb CP-1414S Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital

Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam

Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate

Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin

Imidazoles	Etomidate Metomidate Propoxate

Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin

Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea

Neuroactive steroids	Acebrochol Allopregnanolone (SAGE-547) Alfadolone Alfaxalone Anabolic steroids 3α-Androstanediol Androstenol Androsterone Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 P1-185 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423; Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone; Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem; Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon; Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684

Phenols	Fospropofol Propofol Thymol

Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164

Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether

Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Nicotinamide (niacinamide) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site PAMs: MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: GABAergics

v t e Ergolines

Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine

Psychedelic lysergamides	1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 Ergonovine ETH-LAD IP-LAD LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine Methylisopropyllysergamide MLD-41 PARGY-LAD PRO-LAD

Other ergolines	Ergoline

Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

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案内

dihydroergocryptine