p-ヒドロキシノルエフェドリン
WordNet
- send a message from one computer to another to check whether it is reachable and active; "ping your machine in the office"
- a sharp high-pitched resonant sound (as of a sonar echo or a bullet striking metal)
- contact, usually in order to remind of something; "Ill ping my accountant--April 15 is nearing"
- hit with a pinging noise; "The bugs pinged the lamp shade"
- make a short high-pitched sound; "the bullet pinged when they struck the car"
- the 16th letter of the Roman alphabet (同)p
PrepTutorEJDIC
- (小銃弾などの)ピュー(ブーン)という音 / ピュー(ブーン)と音がする
- parking
- phosphorusの化学記号
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/04/21 18:59:11」(JST)
[Wiki en表示]
p-Hydroxynorephedrine
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| Identifiers |
IUPAC name
- 4-(2-amino-1-hydroxypropyl)phenol
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| Synonyms |
4-Hydroxynorephedrine
para-Hydroxynorephedrine |
| CAS Number |
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| PubChem CID |
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| ChemSpider |
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| Chemical and physical data |
| Formula |
C9H13NO2 |
| Molar mass |
167.21 g/mol |
InChI
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InChI=1S/C9H13NO2/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-6,9,11-12H,10H2,1H3
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Key:JAYBQRKXEFDRER-UHFFFAOYSA-N
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p-Hydroxynorephedrine, or 4-hydroxynorephedrine, is the para-hydroxy analog of norephedrine and an active sympathomimetic metabolite of amphetamine in humans.[1][2] When it occurs as a metabolite of amphetamine, it is produced from both p-hydroxyamphetamine and norephedrine.[2][3][4]
Contents
- 1 Amphetamine metabolism
- 2 See also
- 3 Reference notes
- 4 References
- 5 External links
Amphetamine metabolism
Metabolic pathways of amphetamine in humans[sources 1]
4-Hydroxyphenylacetone
Phenylacetone
Benzoic acid
Hippuric acid
Amphetamine
Norephedrine
4-Hydroxyamphetamine
4-Hydroxynorephedrine
Para-
Hydroxylation
Para-
Hydroxylation
Para-
Hydroxylation
CYP2D6
CYP2D6
unidentified
Beta-
Hydroxylation
Beta-
Hydroxylation
DBH
DBH
Oxidative
Deamination
FMO3
Oxidation
unidentified
Glycine
Conjugation
XM-ligase
GLYAT
In humans, para-hydroxynorephedrine is a metabolite of amphetamine. The hydroxylation of the substituted amphetamines in this image is mediated by CYP2D6 and dopamine β-hydroxylase.
See also
Reference notes
- ^ [5][6][7][8][9][10][11][12][13]
References
- ^ "p-Hydroxynorephedrine". NCBI. PubChem Compound. Retrieved 25 October 2013.
- ^ a b "Adderall XR Prescribing Information" (PDF). Medication Guide. United States Food and Drug Administration. Retrieved 7 October 2013.
- ^ "Amphetamine: Biomedical Effects and Toxicity". NCBI. Pubchem Compound. Retrieved 12 October 2013.
- ^ Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection". J. Pharm. Biomed. Anal. 30 (2): 247–55. doi:10.1016/S0731-7085(02)00330-8. PMID 12191709.
- ^ "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. Shire US Inc. December 2013. pp. 12–13. Retrieved 30 December 2013.
- ^ Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". In Lemke TL, Williams DA, Roche VF, Zito W. Foye's principles of medicinal chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 646–648. ISBN 9781609133450. Retrieved 11 September 2015.
The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39). ... The phase 1 metabolism of amphetamine analogs is catalyzed by two systems: cytochrome P450 and flavin monooxygenase. ... Amphetamine can also undergo aromatic hydroxylation to p-hydroxyamphetamine. ... Subsequent oxidation at the benzylic position by DA β-hydroxylase affords p-hydroxynorephedrine. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.
- ^ Taylor KB (January 1974). "Dopamine-beta-hydroxylase. Stereochemical course of the reaction" (PDF). J. Biol. Chem. 249 (2): 454–458. PMID 4809526. Retrieved 6 November 2014.
Dopamine-β-hydroxylase catalyzed the removal of the pro-R hydrogen atom and the production of 1-norephedrine, (2S,1R)-2-amino-1-hydroxyl-1-phenylpropane, from d-amphetamine.
- ^ Horwitz D, Alexander RW, Lovenberg W, Keiser HR (May 1973). "Human serum dopamine-β-hydroxylase. Relationship to hypertension and sympathetic activity". Circ. Res. 32 (5): 594–599. doi:10.1161/01.RES.32.5.594. PMID 4713201.
Subjects with exceptionally low levels of serum dopamine-β-hydroxylase activity showed normal cardiovascular function and normal β-hydroxylation of an administered synthetic substrate, hydroxyamphetamine.
- ^ Krueger SK, Williams DE (June 2005). "Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism". Pharmacol. Ther. 106 (3): 357–387. doi:10.1016/j.pharmthera.2005.01.001. PMC 1828602. PMID 15922018.
"Table 5: N-containing drugs and xenobiotics oxygenated by FMO"
- ^ Cashman JR, Xiong YN, Xu L, Janowsky A (March 1999). "N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication". J. Pharmacol. Exp. Ther. 288 (3): 1251–1260. PMID 10027866.
- ^ Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection". J. Pharm. Biomed. Anal. 30 (2): 247–255. doi:10.1016/S0731-7085(02)00330-8. PMID 12191709.
- ^ "Substrate/Product". butyrate-CoA ligase. BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014.
- ^ "Substrate/Product". glycine N-acyltransferase. BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014.
External links
- p-Hydroxynorephedrine at the US National Library of Medicine Medical Subject Headings (MeSH)
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Amphetamine
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Main articles
and
pharmaceuticals |
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Amphetamine
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- Adderall
- Adzenys
- Dyanavel
- Evekeo
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Levoamphetamine
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N/A
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Dextroamphetamine
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- Dexedrine
- ProCentra
- Zenzedi
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Lisdexamfetamine
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| Neuropharmacology |
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Biomolecular targets
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- TAAR1 (full agonist)
- CART (mRNA inducer)
- 5-HT1A receptor (low affinity ligand)
- MAO (weak competitive inhibitor)
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|
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Inhibited transporters
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- DAT
- NET
- SERT
- VMAT1
- VMAT2
- EAAT3
- SLC22A3
- SLC22A5
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| Active metabolites |
- 4-Hydroxyamphetamine
- 4-Hydroxynorephedrine
- Norephedrine
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| Related articles |
- ADD
- ADHD
- ADHD management
- Amphetamine psychosis
- Dopamine
- Doping in sport
- Formetorex
- ΔFosB
- History and culture of substituted amphetamines
- History of Benzedrine
- Methamphetamine
- Methylphenidate
- N-Methylphenethylamine
- Narcolepsy
- Nootropic
- Norepinephrine
- Performance-enhancing substance
- Pharmaceutical drug
- Phenethylamine
- Phentermine
- Phenylacetone
- Recreational drug use
- Serotonin
- Substituted amphetamine
- Trace amine
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English Journal
- Toxicity of the amphetamine metabolites 4-hydroxyamphetamine and 4-hydroxynorephedrine in human dopaminergic differentiated SH-SY5Y cells.
- Feio-Azevedo R1, Costa VM2, Ferreira LM3, Branco PS3, Pereira FC4, Bastos ML2, Carvalho F2, Capela JP5.
- Toxicology letters.Toxicol Lett.2017 Mar 5;269:65-76. doi: 10.1016/j.toxlet.2017.01.012. Epub 2017 Jan 20.
- PMID 28115274
- Study on the use of boromycin as a chiral selector in capillary electrophoresis.
- Maier V1, Ranc V, Svidrnoch M, Petr J, Sevčík J, Tesařová E, Armstrong DW.
- Journal of chromatography. A.J Chromatogr A.2012 May 11;1237:128-32. doi: 10.1016/j.chroma.2012.02.073. Epub 2012 Mar 6.
- PMID 22475183
- Central administration of p-hydroxyamphetamine produces a behavioral stimulant effect in rodents: evidence for the involvement of dopaminergic systems.
- Onogi H1, Hozumi M, Nakagawasai O, Arai Y, Ishigaki S, Sato A, Furuta S, Niijima F, Tan-No K, Tadano T.
- Psychopharmacology.Psychopharmacology (Berl).2010 Feb;208(2):323-31. doi: 10.1007/s00213-009-1734-x. Epub 2009 Dec 4.
- PMID 19960188
Japanese Journal
- メタンフェタミン及びその代謝物のパーフルオロアシル誘導体の安定性について
- 井上 堯子,鈴木 真一,丹羽口 徹吉
- 衛生化学 29(6), 412-417, 1983-12-31
- … TFA, PFP and HFB derivatives of methamphetamine, amphetamine and norephedrine were stable, and those of aromatic hydroxylated metabolites were relatively unstable, especially TFA derivatives of p-hydroxynorephedrine was most unstable in these derivatives. …
- NAID 110003643092
- 熱イオン化検出器付ガスクロマトグラフィーによるラット尿中メタンフェタミンとその代謝産物の一斉高感度分析
- 寺田 賢,吉村 三郎,山元 俊憲,吉田 武美,黒岩 幸雄
- 衛生化学 29(3), 143-153, 1983-06-30
- … 0.1 ng, p-hydroxyamphetamine and p-hydroxymethamphetamine were 0.14,0.16 ng, respectively, norephedrine and p-hydroxynorephedrine were 0.26,1.04 ng, respectively. … In the rats, about 89% of the dose of methamphetamine (2.5 mg/kg, i.p.) and 74% of the dose of methamphetamine (5.0 mg/kg, i.p.) were excreted in the 2 days urine. …
- NAID 110003643053
Related Links
- p-Hydroxynorephedrine: p-Hydroxynorephedrine, or 4-hydroxynorephedrine, is the para-hydroxy analog of norephedrine and an active sympathomimetic metabolite of amphetamine in humans.[2][3] When it occurs as a metabolite of ...
- p-HYDROXYNOREPHEDRINE | C9H13NO2 | CID 11099 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and ...
Related Pictures
★リンクテーブル★
[★]
[★]
- 時間単位
- 関
- picosecond、psec
[★]
- 10の-12乗
- 関
- pico