Aniracetam
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Systematic (IUPAC) name |
1-[(4-methoxybenzoyl)]- 2-pyrrolidinone |
Clinical data |
Trade names |
Ampamet, Memodrin, Pergamid |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
Unscheduled |
Routes |
Oral |
Pharmacokinetic data |
Half-life |
1-2.5 hours |
Identifiers |
CAS number |
72432-10-1 N |
ATC code |
N06BX11 |
PubChem |
CID 2196 |
DrugBank |
DB04599 |
ChemSpider |
2111 Y |
UNII |
5L16LKN964 Y |
KEGG |
D01883 Y |
ChEBI |
CHEBI:47943 Y |
ChEMBL |
CHEMBL36994 Y |
Chemical data |
Formula |
C12H13NO3 |
Mol. mass |
219.237 g/mol |
SMILES
- O=C2N(C(=O)c1ccc(OC)cc1)CCC2
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InChI
-
InChI=1S/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3 Y
Key:ZXNRTKGTQJPIJK-UHFFFAOYSA-N Y
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N (what is this?) (verify)
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Aniracetam (Draganon, Sarpul, Ampamet, Memodrin, Referan) is an ampakine and nootropic of the racetam chemical class purported to be considerably more potent than piracetam. It is lipid-soluble and has possible cognition-enhancing effects. It has been tested in animals extensively, Alzheimer's patients, and temporarily-impaired healthy subjects. It has shown potential as an anxiolytic in three clinical animal models. It is sold in Europe as a prescription drug, but can be purchased in most countries without a prescription.
Contents
- 1 Pharmacology
- 2 Side Effects
- 3 Synthesis
- 4 Pharmacokinetics
- 5 See also
- 6 References
- 7 External links
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Pharmacology
After a confirmed test of the anxiolytic efficacy in a mouse model, haloperidol, mecamylamine, and ketanserin were applied to determine the pathways aniracetam depends on to exert its anti-anxiety effects. Haloperidol completely reversed the anxiolytic effects, and mecamylamine and ketanserin nearly completely reversed the effects. This shows that aniracetam's anxiolytic mechanism is facilitated by D2/D3, nACh, and 5-HT2A receptors.[1]
Aniracetam has also been shown to selectively modulate the AMPA receptor[2] and was used as the parent compound to derive a class of drugs known as the ampakines that are being investigated as nootropics and neuroprotective drugs for the treatment of Alzheimer's disease and other neurodegenerative conditions.1
Despite the fat solubility of aniracetam, its half-life is much shorter than that of common racetam analogs such as piracetam.[citation needed]
Commonly used doses are 750-3,000 mg daily usually taken in 2-3 doses.
Side Effects
Common side effects consist of: unrest, anxiety, uneasiness, insomnia. Less common adverse effects include: headaches, somnolence, vertigo, mild epigastric pain, nausea, diarrhea, rash. These effects are generally temporary, and in the studies where they were reported as adverse events, did not require termination of treatment.[3]
Synthesis
The drug was first made in the 1970s by Hoffmann-La Roche.[4][5] Synthesis can be caused by 2-Pyrrolidone reacting with Anisoyl chloride in the presence of Triethylamine.[6]
Alternatively, gamma-Aminobutyric acid can react with anisoyl chloride. Ring closure can be accomplished with the presence of Thionyl chloride.[6]
Pharmacokinetics
The primary metabolites of aniracetam are N-anisoyl-GABA, 2-Pyrrolidone, and Anisic acid.[7]
See also
- Ampakine
- Racetam
- Nootropic
References
- ^ Nakamura K; Kurasawa M (May 2001). "Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism". Eur J Pharmacol. (Kanagawa, Japan). 420 (1): 33–43. doi:10.1016/S0014-2999(01)01005-6. PMID 11412837.
- ^ Ito et al. J. Physiol. 1990; 424: 533-543.
- ^ "Aniracetam: Smarter Nootropics". March 20, 2012. http://www.smarternootropics.com/table-of-contents/aniracetam/. Retrieved April 11, 2012.
- ^ Patent EP 5 143 Hoffmann-La Roche 1978.
- ^ Patent EP 44 088 Hoffmann-La Roche 1978.
- ^ a b A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications, 4. Auflage, Thieme 2001, ISBN 3-13-115134-X.
- ^ abstract at PMID 8199398
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (February 2010) |
External links
- The Cognitive Enhancement Research Institute
Nootropics (N06B)
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Acetylcholinesterases |
- Donepezil
- Galantamine
- Huperzine A (Huperzia Serrata)
- Ladostigil
- Rivastigmine
- Tacrine
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Ampakines |
- CX-516
- CX-546
- CX-614
- CX-691
- CX-717
- IDRA-21
- LY-404,187
- LY-503,430
- PEPA
- Sunifiram
- Unifiram
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D1 Agonists |
- 6-Br-APB
- A-77636
- Dihydrexidine
- Dinapsoline
- Doxanthrine
- SKF-81297
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Eugeroics |
- Adrafinil
- Armodafinil
- Modafinil
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GABAA α5 Inverse Agonists |
- α5IA
- L-655,708
- PWZ-029
- Suritozole
- TB-21007
- ZK-93426
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H3 Antagonists |
- A-349,821
- ABT-239
- Ciproxifan
- GSK-189,254
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mACh Agonists |
- Alvameline
- Arecoline
- Cevimeline
- CI-1017
- Milameline
- Sabcomeline
- Talsaclidine
- Tazomeline
- Xanomeline
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nACh Agonists |
- AR-R17779
- Ispronicline
- Nicotine
- PNU-282,987
- SSR-180,711
- WAY-317,538
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Racetams |
- Aniracetam
- Brivaracetam
- Coluracetam
- Etiracetam
- Fasoracetam
- Levetiracetam
- Nebracetam
- Nefiracetam
- Oxiracetam
- Phenylpiracetam
- Piracetam
- Pramiracetam
- Rolziracetam
- Seletracetam
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Others |
- Acetylcarnitine
- Adafenoxate
- Bifemelane
- Bilobalide (Ginkgo Biloba)
- Carbenoxolone
- Cerlapirdine
- Choline (Lecithin)
- Citicoline
- Cyprodenate
- Dimethylethanolamine
- Ensaculin
- Fipexide
- Idebenone
- Indeloxazine
- Latrepirdine
- Leteprinim
- Linopirdine
- Meclofenoxate
- Nizofenone
- Pirisudanol
- Pyritinol
- S-17092
- Sulbutiamine
- Taltirelin
- Teniloxazine
- Tricyanoaminopropene
- Vinpocetine
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Glutamatergics
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Ionotropic |
AMPA
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- Agonists: 5-Fluorowillardiine
- AMPA
- Domoic acid
- Quisqualic acid; Positive allosteric modulators: Aniracetam
- Cyclothiazide
- CX-516
- CX-546
- CX-614
- CX-691
- CX-717
- Diazoxide
- HCTZ
- IDRA-21
- LY-392,098
- LY-404,187
- LY-451,395
- LY-451,646
- LY-503,430
- Org 26576
- Oxiracetam
- PEPA
- Piracetam
- Pramiracetam
- S-18986
- Sunifiram
- Unifiram
Antagonists: ATPO
- Barbiturates
- BGG492
- Caroverine
- CNQX
- DNQX
- GYKI-52466
- NBQX
- Perampanel
- Talampanel
- Tezampanel
- Topiramate; Negative allosteric modulators: GYKI-53,655
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NMDA
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- Agonists: Glutamate/acite site competitive agonists: Aspartate
- Glutamate
- Homoquinolinic acid
- Ibotenic acid
- NMDA
- Quinolinic acid
- Tetrazolylglycine; Glycine site agonists: ACBD
- ACPC
- ACPD
- Alanine
- CCG
- Cycloserine
- DHPG
- Fluoroalanine
- Glycine
- GLYX-13
- HA-966
- L-687,414
- Milacemide
- Sarcosine
- Serine
- Tetrazolylglycine; Polyamine site agonists: Acamprosate
- Spermidine
- Spermine
Antagonists: Competitive antagonists: AP5 (APV)
- AP7
- CGP-37849
- CGP-39551
- CGP-39653
- CGP-40116
- CGS-19755
- CPP
- LY-233,053
- LY-235,959
- LY-274,614
- MDL-100,453
- Midafotel (d-CPPene)
- NPC-12,626
- NPC-17,742
- PBPD
- PEAQX
- Perzinfotel
- PPDA
- SDZ-220581
- Selfotel; Noncompetitive antagonists: ARR-15,896
- Caroverine
- Dexanabinol
- FPL-12495
- FR-115,427
- Hodgkinsine
- Magnesium
- MDL-27,266
- NPS-1506
- Psychotridine
- Zinc; Uncompetitive pore blockers: 2-MDP
- 3-MeO-PCP
- 8A-PDHQ
- Alaproclate
- Amantadine
- Aptiganel
- ARL-12,495
- ARL-15,896-AR
- ARL-16,247
- Budipine
- Delucemine
- Dexoxadrol
- Dextrallorphan
- Dieticyclidine
- Dizocilpine
- Endopsychosin
- Esketamine
- Etoxadrol
- Eticyclidine
- Gacyclidine
- Ibogaine
- Indantadol
- Ketamine
- Ketobemidone
- Lanicemine
- Loperamide
- Memantine
- Meperidine (Pethidine)
- Methadone (Levomethadone)
- Methorphan (Dextromethorphan
- Levomethorphan)
- Methoxetamine
- Milnacipran
- Morphanol (Dextrorphan
- Levorphanol)
- NEFA
- Neramexane
- Nitrous oxide
- Noribogaine
- Orphenadrine
- PCPr
- Phencyclamine
- Phencyclidine
- Propoxyphene
- Remacemide
- Rhynchophylline
- Riluzole
- Rimantadine
- Rolicyclidine
- Sabeluzole
- Tenocyclidine
- Tiletamine
- Tramadol
- Xenon; Glycine site antagonists: ACEA-1021
- ACEA-1328
- ACPC
- Carisoprodol
- CGP-39653
- CKA
- DCKA
- Felbamate
- Gavestinel
- GV-196,771
- Kynurenic acid
- L-689,560
- L-701,324
- Lacosamide
- Licostinel
- LU-73,068
- MDL-105,519
- Meprobamate
- MRZ 2/576
- PNQX
- ZD-9379; NR2B subunit antagonists: Besonprodil
- CO-101,244 (PD-174,494)
- CP-101,606
- Eliprodil
- Haloperidol
- Ifenprodil
- Isoxsuprine
- Nylidrin
- Ro8-4304
- Ro25-6981
- Traxoprodil; Polyamine site antagonists: Arcaine
- Co 101676
- Diaminopropane
- Acamprosate
- Diethylenetriamine
- Huperzine A
- Putrescine
- Ro 25-6981; Unclassified/unsorted antagonists: Chloroform
- Diethyl ether
- Enflurane
- Ethanol (Alcohol)
- Halothane
- Isoflurane
- Methoxyflurane
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Xylene
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Kainate
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- Agonists: 5-Iodowillardiine
- ATPA
- Domoic acid
- Kainic acid
- LY-339,434
- SYM-2081
Antagonists: BGG492
- CNQX
- DNQX
- LY-382,884
- NBQX
- NS102
- Tezampanel
- Topiramate
- UBP-302; Negative allosteric modulators: NS-3763
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Metabotropic |
Group I
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- Agonists: Non-selective: ACPD
- DHPG
- Quisqualic acid; mGlu1-selective: Ro01-6128
- Ro67-4853
- Ro67-7476
- VU-71; mGlu5-selective: ADX-47273
- CDPPB
- CHPG
- DFB
- VU-1545
Antagonists: Non-selective: MCPG
- NPS-2390; mGlu1-selective: BAY 36-7620
- CPCCOEt
- LY-367,385
- LY-456,236; mGlu5-selective: CTEP
- Dipraglurant
- DMeOB
- LY-344,545
- SIB-1757
- SIB-1893; Negative allosteric modulators: Fenobam
- MPEP
- MTEP
- GRN-529
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Group II
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- Agonists: Non-selective: CBiPES
- DCG-IV
- Eglumegad
- LY-379,268
- LY-404,039
- LY-487,379
- MGS-0028; mGlu2-selective: BINA
- LY-566,332
Antagonists: Non-selective: APICA
- EGLU
- HYDIA
- LY-307,452
- LY-341,495
- MCPG
- MGS-0039: mGlu2-selective: PCCG-4; mGlu3-selective: CECXG; Negative allosteric modulators: RO4491533
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Group III
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- Agonists: Non-selective: L-AP4; mGlu4-selective: PHCCC
- VU-001,171
- VU-0155,041; mGlu7-selective: AMN082; mGlu8-selective: DCPG
Antagonists: Non-selective: CPPG
- MAP4
- MSOP
- MPPG
- MTPG
- UBP-1112; mGlu7-selective: MMPIP
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Transporter
inhibitors |
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Others |
Precursors
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Cofactors
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- α-Ketoglutaric acid
- Iron
- Sulfur
- Vitamin B2 (as FAD and FMN)
- Vitamin B3 (as NADPH)
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Others
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Racetams
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- Aloracetam
- Aniracetam
- Brivaracetam
- Cebaracetam
- Coluracetam
- Dimiracetam
- Doliracetam
- Dupracetam
- Etiracetam/Levetiracetam
- Fasoracetam
- Imuracetam
- Molracetam
- Nebracetam
- Nefiracetam
- Noopept
- Oxiracetam
- Phenylpiracetam
- Piperacetam
- Piracetam
- Pramiracetam
- Rolipram
- Rolziracetam
- Seletracetam
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