Substituerede amfetaminer

Substituerede amfetaminer eller amfetaminer er en klasse af kemiske stoffer baseret på amfetamins struktur.^[1] Den omfatter alle derivater som er dannet ved at erstatte eller substituere et eller flere brintatomer i amfetamin med substituenter.^[1]^[2]^[3]^[4] Forbindelserne i denne gruppe spænder over en række farmakologiske midler, herunder stimulanter, empatogener og hallucinogener og andre.^[2] Eksempler på substituerede amfetaminer er amfetamin,^[1]^[2] metamfetamin,^[1] efedrin,^[1] cathinon,^[1] fentermin,^[1] mefentermin,^[1] bupropion,^[1] methoxyfenamin,^[1] selegilin,^[1] amfepramon,^[1] pyrovaleron,^[1] MDMA (ecstasy) og DOM (STP).

Nogle af amfetamins substituerede derivater forekommer i naturen, for eksempel i bladene på ledris- og khat-planter, som har været brugt af mennesker i mere end 1000 år for deres farmakologiske virkninger.^[1] Amfetamin blev først fremstillet i slutningen af det 19. århundrede. I 1930'erne fandt amfetamin og nogle af dets derivater brug som anti-kongestanter i symptomatisk behandling af forkølelse og også lejlighedsvis som psykoaktive midler. Deres virkninger på centralnervesystemet er forskelligartede, men kan opsummeres ved tre overlappende typer aktivitet: psykoanaleptisk, hallucinogen og empatogen. Forskellige substituerede amfetaminer kan forårsage disse virkninger enten separat eller i kombination.

Eksempler

Amfetaminer er selv en undergruppe af substituerede phenethylamin-forbindelser. Substitution af brintatomer resulterer i en stor klasse af kemiske forbindelser. Typisk reaktioner er substitution med methyl- og nogle gange ethylgrupper på amin- og fenylgrupperne:^[5]^[6]^[7]

Stof	Substituenter
	N	α	β	fenylgruppe
	N	α	β	2	3	4	5
Phenethylamin
Amfetamin (α-methylphenylethylamine)		-CH₃
Metamfetamin (N-metylamfetamin)	-CH₃	-CH₃
Fentermin (α-metylamfetamin)		-(CH₃)₂
Efedrin	-CH₃	-CH₃	-OH
Pseudoefedrin	-CH₃	-CH₃	-OH
Cathinon		-CH₃	=O
Metcathinon (efedron)	-CH₃	-CH₃	=O
MDA (3,4-methylenedioxyamphetamine)		-CH₃			-O-CH₂-O-
MDMA (3,4-metylenedioxymethamfetamin)	-CH₃	-CH₃			-O-CH₂-O-
MDEA (3,4-metylenedioxy-N-etylamfetamin)	-CH₂-CH₃	-CH₃			-O-CH₂-O-
EDMA (3,4-etylenedioxy-N-metylamfetamin)	-CH₃	-CH₃			-O-CH₂-CH₂-O-
MBDB (N-metyl-1,3-benzodioxolylbutanamin)	-CH₃	-CH₂-CH₃			-O-CH₂-O-
PMA (para-methoxyamfetamin)		-CH₃				-O-CH₃
PMMA (para-metoxymetamfetamin)	-CH₃	-CH₃				-O-CH₃
4-MTA (4-metylthioamfetamin)		-CH₃				-S-CH₃
3,4-DMA (3,4-dimetoxyamfetamin)		-CH₃			-O-CH₃	-O-CH₃
3,4,5-trimetoxyamfetamin (α-metylmescalin)		-CH₃			-O-CH₃	-O-CH₃	-O-CH₃
DOM (2,5-dimethoxy-4-metylamfetamin)		-CH₃		-O-CH₃		-CH₃	-O-CH₃
DOB (2,5-dimethoxy-4-bromoamfetamin)		-CH₃		-O-CH₃		-Br	-O-CH₃

Referencer

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Hagel JM, Krizevski R, Marsolais F, Lewinsohn E, Facchini PJ (2012). "Biosynthesis of amphetamine analogs in plants". Trends Plant Sci. 17 (7): 404-412. doi:10.1016/j.tplants.2012.03.004. 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.
^ ^a ^b ^c Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". Foye's principles of medicinal chemistry (7th udgave). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. s. 646-648. 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).
^ Lillsunde P, Korte T (marts 1991). "Determination of ring- and N-substituted amphetamines as heptafluorobutyryl derivatives". Forensic Sci. Int. 49 (2): 205-213. doi:10.1016/0379-0738(91)90081-s. PMID 1855720.
^ Custodio, Raly James Perez; Botanas, Chrislean Jun; Yoon, Seong Shoon; Peña, June Bryan de la; Peña, Irene Joy dela; Kim, Mikyung; Woo, Taeseon; Seo, Joung-Wook; Jang, Choon-Gon; Kwon, Yong Ho; Kim, Nam Yong (2017-11-01). "Evaluation of the Abuse Potential of Novel Amphetamine Derivatives with Modifications on the Amine (NBNA) and Phenyl (EDA, PMEA, 2-APN) Sites". Biomolecules & Therapeutics (engelsk). 25 (6): 578-585. doi:10.4062/biomolther.2017.141. ISSN 2005-4483. PMC 5685426. PMID 29081089.
^ Goldfrank, s. 1125-1127
^ Glennon, s. 184-187
^ Schatzberg, s. 843

Bibliografi

Ghodse, Hamid (2002). Drugs and Addictive Behaviour. A Guide to Treatment. 3rd Edition. Cambridge University Press. s. 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. ISBN 978-0-07-160405-5. (Webside ikke længere tilgængelig)
Ledgard, Jared (2007). A Laboratory History of Narcotics. Volume 1. Amphetamines and Derivatives. Jared Ledgard. s. 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.

Infoboks uden skabelon

Denne artikel har en infoboks dannet af en tabel eller tilsvarende.

[Amphetamine_-_a_substituted_amphetamine-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Hagel JM, Krizevski R, Marsolais F, Lewinsohn E, Facchini PJ (2012). "Biosynthesis of amphetamine analogs in plants". Trends Plant Sci. 17 (7): 404-412. doi:10.1016/j.tplants.2012.03.004. 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.

[Substituted_amphetamines-2] Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". Foye's principles of medicinal chemistry (7th udgave). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. s. 646-648. 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).

[pmid1855720-3] Lillsunde P, Korte T (marts 1991). "Determination of ring- and N-substituted amphetamines as heptafluorobutyryl derivatives". Forensic Sci. Int. 49 (2): 205-213. doi:10.1016/0379-0738(91)90081-s. PMID 1855720.

[4] Custodio, Raly James Perez; Botanas, Chrislean Jun; Yoon, Seong Shoon; Peña, June Bryan de la; Peña, Irene Joy dela; Kim, Mikyung; Woo, Taeseon; Seo, Joung-Wook; Jang, Choon-Gon; Kwon, Yong Ho; Kim, Nam Yong (2017-11-01). "Evaluation of the Abuse Potential of Novel Amphetamine Derivatives with Modifications on the Amine (NBNA) and Phenyl (EDA, PMEA, 2-APN) Sites". Biomolecules & Therapeutics (engelsk). 25 (6): 578-585. doi:10.4062/biomolther.2017.141. ISSN 2005-4483. PMC 5685426. PMID 29081089.

[5] Goldfrank, s. 1125-1127

[6] Glennon, s. 184-187

[ref16-7] Schatzberg, s. 843

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Substituerede amfetaminer

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Optiske isomerer af amfetamin


L-ampfetamin	D-ampfetamin