Substituted amphetamine
Substituted amphetamine | ||
---|---|---|
Chemical class Substituted derivatives of amphetamine | | |
Legal status | ||
In Wikidata |
L-amphetamine | D-amphetamine |
Substituted amphetamines are a
Some of amphetamine's substituted
Partial list of substituted amphetamines
Generic or Trivial Name | Chemical Name | # of Subs |
---|---|---|
Amphetamine | α-Methyl-phenethylamine | 0 |
Methamphetamine | N-Methylamphetamine | 1 |
Ethylamphetamine | N-Ethylamphetamine | 1 |
Propylamphetamine | N-Propylamphetamine | 1 |
Isopropylamphetamine | N-iso-Propylamphetamine | 1 |
Phentermine | α-Methylamphetamine | 1 |
Phenylpropanolamine (PPA) | β-Hydroxyamphetamine, (1R,2S)- | 1 |
Cathine | β-Hydroxyamphetamine, (1S,2S)- | 1 |
Cathinone | β-Ketoamphetamine | 1 |
Ortetamine | 2-Methylamphetamine | 1 |
2-Fluoroamphetamine (2-FA) | 2-Fluoroamphetamine | 1 |
3-Methylamphetamine (3-MA) | 3-Methylamphetamine | 1 |
2-Phenyl-3-aminobutane | 2-Phenyl-3-aminobutane | 1 |
Tranylcypromine | Trans-2-phenylcyclopropylamine | |
3-Fluoroamphetamine (3-FA) | 3-Fluoroamphetamine | 1 |
Norfenfluramine | 3-Trifluoromethylamphetamine | 1 |
4-Methylamphetamine (4-MA) | 4-Methylamphetamine | 1 |
para-Methoxyamphetamine (PMA) | 4-Methoxyamphetamine | 1 |
para-Ethoxyamphetamine | 4-Ethoxyamphetamine | 1 |
4-Methylthioamphetamine (4-MTA) | 4-Methylthioamphetamine | 1 |
Norpholedrine (α-Me-TRA) |
4-Hydroxyamphetamine | 1 |
para-Bromoamphetamine (PBA, 4-BA) | 4-Bromoamphetamine | 1 |
para-Chloroamphetamine (PCA, 4-CA) | 4-Chloroamphetamine | 1 |
para-Fluoroamphetamine (PFA, 4-FA, 4-FMP) |
4-Fluoroamphetamine | 1 |
para-Iodoamphetamine (PIA, 4-IA) | 4-Iodoamphetamine | 1 |
Clobenzorex | N-(2-chlorobenzyl)-1-phenylpropan-2-amine | 1 |
Dimethylamphetamine | N,N-Dimethylamphetamine | 2 |
Benzphetamine | N-Benzyl-N-methylamphetamine | 2 |
D-Deprenyl | N-Methyl-N-propargylamphetamine, (S)- | 2 |
Selegiline | N-Methyl-N-propargylamphetamine, (R)- | 2 |
Mephentermine | N-Methyl-α-methylamphetamine | 2 |
Phenpentermine |
α,β-Dimethylamphetamine | 2 |
Ephedrine | β-Hydroxy-N-methylamphetamine, (1R,2S)- | 2 |
Pseudoephedrine (PSE) | β-Hydroxy-N-methylamphetamine, (1S,2S)- | 2 |
Methcathinone | β-Keto-N-methylamphetamine | 2 |
Ethcathinone | β-Keto-N-ethylamphetamine | 2 |
Clortermine | 2-Chloro-α-methylamphetamine | 2 |
Methoxymethylamphetamine (MMA) |
3-Methoxy-4-methylamphetamine | 2 |
Fenfluramine | 3-Trifluoromethyl-N-ethylamphetamine | 2 |
Dexfenfluramine | 3-Trifluoromethyl-N-ethylamphetamine, (S)- | 2 |
4-Methylmethamphetamine (4-MMA) |
4-Methyl-N-methylamphetamine | 2 |
para-Methoxymethamphetamine (PMMA) |
4-Methoxy-N-methylamphetamine | 2 |
para-Methoxyethylamphetamine (PMEA) |
4-Methoxy-N-ethylamphetamine | 2 |
Pholedrine | 4-Hydroxy-N-methylamphetamine | 2 |
Chlorphentermine | 4-Chloro-α-methylamphetamine | 2 |
para-Fluoromethamphetamine (PFMA, 4-FMA) |
4-Fluoro-N-methylamphetamine | 2 |
Xylopropamine | 3,4-Dimethylamphetamine | 2 |
α-Methyldopamine (α-Me-DA) | 3,4-Dihydroxyamphetamine | 2 |
3,4-Methylenedioxyamphetamine (MDA) | 3,4-Methylenedioxyamphetamine | 2 |
Dimethoxyamphetamine (DMA) | X,X-Dimethoxyamphetamine | 2 |
6-APB | 6-(2-aminopropyl)benzofuran | 2 |
Nordefrin (α-Me-NE) |
β,3,4-Trihydroxyamphetamine, (R)- | 3 |
Oxilofrine | β,4-Dihydroxy-N-methylamphetamine | 3 |
Aleph | 2,5-dimethoxy-4-methylthioamphetamine | 3 |
Dimethoxybromoamphetamine (DOB) |
2,5-Dimethoxy-4-bromoamphetamine | 3 |
Dimethoxychloroamphetamine (DOC) |
2,5-Dimethoxy-4-chloroamphetamine | 3 |
Dimethoxyfluoroethylamphetamine (DOEF) |
2,5-Dimethoxy-4-fluoroethylamphetamine | 3 |
Dimethoxyethylamphetamine (DOET) |
2,5-Dimethoxy-4-ethylamphetamine | 3 |
Dimethoxyfluoroamphetamine (DOF) |
2,5-Dimethoxy-4-fluoroamphetamine | 3 |
Dimethoxyiodoamphetamine (DOI) |
2,5-Dimethoxy-4-iodoamphetamine | 3 |
Dimethoxymethylamphetamine (DOM) |
2,5-Dimethoxy-4-methylamphetamine | 3 |
Dimethoxynitroamphetamine (DON) |
2,5-Dimethoxy-4-nitroamphetamine | 3 |
Dimethoxypropylamphetamine (DOPR) |
2,5-Dimethoxy-4-propylamphetamine | 3 |
Dimethoxytrifluoromethylamphetamine (DOTFM) |
2,5-Dimethoxy-4-trifluoromethylamphetamine | 3 |
Methylenedioxymethamphetamine (MDMA) | 3,4-Methylenedioxy-N-methylamphetamine | 3 |
Methylenedioxyethylamphetamine (MDEA) |
3,4-Methylenedioxy-N-ethylamphetamine | 3 |
Methylenedioxyhydroxyamphetamine (MDOH) |
3,4-Methylenedioxy-N-hydroxyamphetamine | 3 |
2-Methyl-MDA | 3,4-Methylenedioxy-2-methylamphetamine | 3 |
5-Methyl-MDA | 4,5-Methylenedioxy-3-methylamphetamine | 3 |
Methoxymethylenedioxyamphetamine (MMDA) |
3-Methoxy-4,5-methylenedioxyamphetamine | 3 |
Trimethoxyamphetamine (TMA) | X,X,X-Trimethoxyamphetamine | 3 |
Dimethylcathinone |
β-Keto-N,N-dimethylamphetamine | 3 |
Diethylcathinone |
β-Keto-N,N-diethylamphetamine | 3 |
Bupropion | β-Keto-3-chloro-N-tert-butylamphetamine | 3 |
Mephedrone (4-MMC) | β-Keto-4-methyl-N-methylamphetamine | 3 |
Methedrone (PMMC) | β-Keto-4-methoxy-N-methylamphetamine | 3 |
Brephedrone (4-BMC) |
β-Keto-4-bromo-N-methylamphetamine | 3 |
Flephedrone (4-FMC) | β-Keto-4-fluoro-N-methylamphetamine | 3 |
Prodrugs of amphetamine/methamphetamine
A variety of
Structure
diethylpropion, desmethylselegiline, and benzphetamine from this table.[7]. You can help by adding to it . (February 2019) |
Amphetamines are a subgroup of the
Substance | Substituents | Structure | Sources | ||||||
---|---|---|---|---|---|---|---|---|---|
N | α | β | phenyl group | ||||||
2 | 3 | 4 | 5 | ||||||
Phenethylamine | |||||||||
Amphetamine (α-methylphenylethylamine) | -CH3 | [7] | |||||||
Methamphetamine (N-methylamphetamine) | -CH3 | -CH3 | [7] | ||||||
Phentermine (α-methylamphetamine) | -(CH3)2 | [7] | |||||||
Ephedrine | -CH3 | -CH3 | -OH | [7] | |||||
Pseudoephedrine | -CH3 | -CH3 | -OH | [7] | |||||
Cathinone | -CH3 | =O | [7] | ||||||
Methcathinone (ephedrone) | -CH3 | -CH3 | =O | [7] | |||||
MDA (3,4-methylenedioxyamphetamine) | -CH3 | -O-CH2-O- | [7] | ||||||
MDMA (3,4-methylenedioxymethamphetamine) | -CH3 | -CH3 | -O-CH2-O- | [7] | |||||
MDEA (3,4-methylenedioxy-N-ethylamphetamine)
|
-CH2-CH3 | -CH3 | -O-CH2-O- | [7] | |||||
EDMA (3,4-ethylenedioxy-N-methylamphetamine) | -CH3 | -CH3 | -O-CH2-CH2-O- | ||||||
MBDB (N-methyl-1,3-benzodioxolylbutanamine) | -CH3 | -CH2-CH3 | -O-CH2-O- | ||||||
PMA (para-methoxyamphetamine) | -CH3 | -O-CH3 | |||||||
PMMA (para-methoxymethamphetamine)
|
-CH3 | -CH3 | -O-CH3 | ||||||
4-MTA (4-methylthioamphetamine)
|
-CH3 | -S-CH3 | |||||||
3,4-DMA (3,4-dimethoxyamphetamine) | -CH3 | -O-CH3 | -O-CH3 | ||||||
3,4,5-Trimethoxyamphetamine (α-methylmescaline) | -CH3 | -O-CH3 | -O-CH3 | -O-CH3 | |||||
DOM (2,5-dimethoxy-4-methylamphetamine)
|
-CH3 | -O-CH3 | -CH3 | -O-CH3 | |||||
DOB (2,5-dimethoxy-4-bromoamphetamine) | -CH3 | -O-CH3 | -Br | -O-CH3 |
History
During World War II, amphetamines were used by the German military to keep their tank crews awake for long periods, and treat depression. It was noticed that extended rest was required after such artificially induced activity.[12] The widespread use of substituted amphetamines began in postwar Japan and quickly spread to other countries. Modified "designer amphetamines", such as MDA and PMA, have gained in popularity since the 1960s.[15] In 1970, the United States adopted "the Controlled Substances Act" that limited non-medical use of substituted amphetamines.[15] Street use of PMA was noted in 1972.[16] MDMA emerged as a substitute for MDA in the early 1970s.[17] American chemist Alexander Shulgin first synthesized the drug in 1976 and through him the drug was briefly introduced into psychotherapy.[18] Recreational use grew and in 1985 MDMA was banned by the US authorities in an emergency scheduling initiated by the Drug Enforcement Administration.[19]
Since the mid-1990s, MDMA has become a popular
Legal status
Agents | Legal status by 2009.[22][23][24][25] | |||
---|---|---|---|---|
US | Russia | Australia | ||
racemic )
|
Schedule II | Schedule II | Schedule II | Schedule 8 |
Dextroamphetamine (D-amphetamine) | Schedule II | Schedule II | Schedule I | Schedule 8 |
Levoamphetamine (L-amphetamine) | Schedule II | Schedule II | Schedule III | Schedule 8 |
Methamphetamine | Schedule II | Schedule II | Schedule I | Schedule 8 |
Cathinone Methcathinone | Schedule I | Schedule I | Schedule I | Schedule 9 |
MDEA
|
Schedule I | Schedule I | Schedule I | Schedule 9 |
PMA | Schedule I | Schedule I | Schedule I | Schedule 9 |
DOM, 3,4,5-TMA
|
Schedule I | Schedule I | Schedule I | Schedule 9 |
See also
- Substituted phenethylamines
- Substituted methylenedioxyphenethylamines
- Substituted cathinones
- Substituted phenylmorpholines
- 2Cs, DOx, 25-NB
- Substituted tryptamines
- Substituted α-alkyltryptamines
- D-Deprenyl, MAO-B inhibitor prodrug that metabolizes into both D-amphetamine and D-methamphetamine
- Amphetaminil, brand name Aponeuron a largely-market-withdrawn (due to abuse liability) amphetamine
References
- ^ PMID 22502775.
Substituted amphetamines, which are also called phenylpropylamino alkaloids, are a diverse group of nitrogen-containing compounds that feature a phenethylamine backbone with a methyl group at the α-position relative to the nitrogen (Figure 1). Countless variation in functional group substitutions has yielded a collection of synthetic drugs with diverse pharmacological properties as stimulants, empathogens and hallucinogens [3]. ... Beyond (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine, myriad other substituted amphetamines have important pharmaceutical applications. The stereochemistry at the α-carbon is often a key determinant of pharmacological activity, with (S)-enantiomers being more potent. For example, (S)-amphetamine, commonly known as d-amphetamine or dextroamphetamine, displays five times greater psychostimulant activity compared with its (R)-isomer [78]. Most such molecules are produced exclusively through chemical syntheses and many are prescribed widely in modern medicine. For example, (S)-amphetamine (Figure 4b), a key ingredient in Adderall and Dexedrine, is used to treat attention deficit hyperactivity disorder (ADHD) [79]. ...
[Figure 4](b) Examples of synthetic, pharmaceutically important substituted amphetamines. - ^ ISBN 9781609133450.
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).
- PMID 1855720.
- PMID 29081089.
- S2CID 4913721.
- ISBN 978-3-642-38818-7.
- ^ ISBN 9781118106051. Retrieved 16 February 2019.
- ^ Goldfrank, pp. 1125–1127
- ^ Glennon, pp. 184–187
- ^ Schatzberg, p.843
- ISBN 978-0-471-49640-3.
- ^ a b c Snow, p. 1
- S2CID 1786307.
- ^ Goldfrank, p. 1125
- ^ a b c d Goldfrank, p. 1119
- from the original on 26 November 2009.
- ^ Foderaro, Lisa W. (11 December 1988). "Psychedelic Drug Called Ecstasy Gains Popularity in Manhattan Nightclubs". The New York Times. Archived from the original on 17 November 2015. Retrieved 27 August 2015.
- PMID 20653618.
- ^ Snow, p. 71
- ^ Goldfrank, p. 1121
- PMID 20643699.
- ^ "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. August 2003. Archived from the original on 25 November 2010.
{{cite web}}
: CS1 maint: unfit URL (link) May 2010 Edition Archived 24 December 2012 at the Wayback Machine - ^ "DEA Drug Scheduling". U.S. Drug Enforcement Administration. Archived from the original on 7 February 2011. Retrieved 17 November 2009.
- ^ "Resolution of RF Government of 30 June 1998 N 681 "On approval of list of drugs psychotropic substances and their precursors subject to control in the Russian Federation"". garant.ru (in Russian). Archived from the original on 20 January 2012. Retrieved 15 November 2009.
- ^ "The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP)". Australian Therapeutic Goods Administration (TGA). Archived from the original on 27 June 2015. Retrieved 26 June 2015.
- ^ "Convention on Psychotropic Substances, 1971" (PDF). United Nations. Archived from the original on 25 November 2010.
{{cite web}}
: CS1 maint: unfit URL (link)
Bibliography
- Ghodse, Hamid (2002). Drugs and Addictive Behaviour. A Guide to Treatment. 3rd Edition. Cambridge University Press. p. 501. ISBN 978-0-511-05844-8.
- Glennon, Richard A. (2008). "Neurobiology of Hallucinogens". The American Psychiatric Publishing textbook of substance abuse treatment. American Psychiatric Publishing. ISBN 978-1-58562-276-4.
- Goldfrank, Lewis R. & Flomenbaum, Neal (2006). Goldfrank's Toxicologic Emergencies, 8th Edition. McGraw Hill. ISBN 978-0-07-147914-1.
- Katzung, Bertram G. (2009). Basic & clinical pharmacology. 11th edition. McGraw-Hill Medical. ]
- Ledgard, Jared (2007). A Laboratory History of Narcotics. Volume 1. Amphetamines and Derivatives. Jared Ledgard. p. 268. ISBN 978-0-615-15694-1.
- Schatzberg, Alan F. & Nemeroff, Charles B. (2009). The American Psychiatric Publishing Textbook of Psychopharmacology. The American Psychiatric Publishing. ISBN 978-1-58562-309-9.
- Snow, Otto (2002). Amphetamine syntheses. Thoth Press. ISBN 978-0-9663128-3-6.
- Veselovskaya NV, Kovalenko AE (2000). Drugs. Properties, effects, pharmacokinetics, metabolism. MA: Triada-X. ISBN 978-5-94497-029-9.
External links
- Media related to Substituted amphetamines at Wikimedia Commons