3C (3C-''x''), also known as 4-substituted 3,5-dimethoxyamphetamines, substituted 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1) analogues, or 3C-scalines, is a general name for the family of

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science ...

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

s containing methoxy groups on the 3 and 5

positions Position often refers to: * Position (geometry), the spatial location (rather than orientation) of an entity * Position, a job or occupation Position may also refer to: Games and recreation * Position (poker), location relative to the dealer * ...

of a

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen ato ...

ring. These

compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struct ...

s are analogues of

3,4,5-trimethoxyamphetamine Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analo ...

(3,4,5-TMA or TMA-1). The 3C drugs are not the amphetamine counterparts of the 2C drugs, which are 4-substituted 2,5-dimethoxyphenethylamines. Instead, the

DOx 4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- positi ...

drugs, which are 4-substituted 2,5-dimethoxyamphetamines, are the amphetamine counterparts of the 2C drugs. The 3C drugs are the amphetamine counterparts of

substituted mescaline analogue A substituted mescaline analogue, also known as a scaline and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an structural analog, analogue of the substituted phenethylamine, phenethylamine serotonergic psychedelic mescal ...

s (4-substituted 3,5-dimethoxyphenethylamines). Moreover, in terms of naming with the "3C" prefix, the 3C drugs are generally actually

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

s of TMA-1 with the 4-position

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

extended rather than having any 4-position

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and '' functional group'', as well as '' ...

. In this regard, they would be the 3,5-dimethoxyamphetamine counterparts of the

2C-O 2,4,5-Trimethoxyphenethylamine (2C-O or 2C-OMe) or is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline (3,4,5-trimethoxy). Chemistry 2C-O is a member of a class of che ...

(2,4,5-trimethoxyphenethylamine) drugs (e.g., 2C-O-4) and the

2,4,5-trimethoxyamphetamine Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs ...

(2,4,5-TMA; TMA-2) derivatives (e.g.,

MEM Mem (also spelled Meem, Meme, or Mim) is the thirteenth letter of the Semitic abjads, including Hebrew mēm , Aramaic Mem , Syriac mīm ܡ, Arabic mīm and Phoenician mēm . Its sound value is . The Phoenician letter gave rise to the Gr ...

). 3C drugs have been developed and/or studied by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamp ...

and Daniel Trachsel, among others. The

pharmacology Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemi ...

of 3C drugs has been studied and described.

List of 3C drugs

4-Methoxylated

3,4,5-Trimethoxyamphetamine Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analo ...

(3,4,5-TMA; TMA-1; 3C-mescaline) *

3C-AL 3C-AL is a psychedelic phenethylamine with structural similarities to allylescaline. Little information exists on the human pharmacology of 3C-AL and it has little-to-no history of human use. It can be synthesized from syringaldehyde by reaction ...

(3C-allylescaline) (4-allyloxy-3,5-dimethoxyamphetamine) *

3C-BZ 3C-BZ (4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', the dosage range is listed as 25–200 mg and the durat ...

(3C-benzscaline) (4-benzyloxy-3,5-dimethoxyamphetamine) * 3C-CPM (3C-cyclopropylmescaline) (4-cyclopropylmethoxy-3,5-dimethoxyamphetamine) *

3C-DFE 3C-DFE is a lesser-known psychedelic drug, which is a fluorinated derivative of 3C-E. It was first synthesised by Daniel Trachsel in 2002, and has been reported as showing similar psychedelic activity to related compounds, with a dose range of ar ...

(3C-difluoroescaline) (4-(2,2-difluoroethoxy)-3,5-dimethoxyamphetamine) * 3C-DFM (3C-difluoromescaline) (4-(2,2-difluoromethoxy)-3,5-dimethoxyamphetamine) *

3C-E 3C-E is a psychedelic of the amphetamine class. It was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', Shulgin lists the dosage range as 30 to 60 mg, consumed orally. The duration of action was stated to be 8–12 hours. T ...

(3C-escaline) (4-ethoxy-3,5-dimethoxyamphetamine) * 3C-FE (3C-fluoroescaline) (4-(2-fluoroethoxy)-3,5-dimethoxyamphetamine) * 3C-FP (3C-fluoroproscaline) (4-(3-fluoropropoxy)-3,5-dimethoxyamphetamine) * 3C-IB (3C-isobuscaline) (4-isobutoxy-3,5-dimethoxyamphetamine) * 3C-IP (3C-isoproscaline) (4-isopropoxy-3,5-dimethoxyamphetamine) *

3C-MAL 3C-MAL is a psychedelic phenethylamine with structural similarities to methallylescaline. Little information exists on the human pharmacology of 3C-MAL and it has little-to-no history of human use. The hydrochloride salt is a white crystal with ...

(3C-methallylescaline) (4-methallyloxy-3,5-dimethoxyamphetamine) *

3C-P 3C-P (α-Methyl-4-propoxy-3,5-dimethoxyphenethylamine) is a psychedelic phenethylamine. It has structural and pharmacodynamic properties similar to the drugs mescaline, proscaline, and amphetamine. Little information exists on the human pharmac ...

(3C-proscaline) (4-propoxy-3,5-dimethoxyamphetamine) * 3C-TFE (3C-trifluoroescaline) (4-(2,2,2-trifluoroethoxy)-3,5-dimethoxyamphetamine)

Other 4-substituted

* 4-Br-3,5-DMA (4-bromo-3,5-dimethoxyamphetamine) * 4-I-3,5-DMA (4-iodo-3,5-dimethoxyamphetamine) * 4-PhPr-3,5-DMA (4-(3-phenylpropyl)-3,5-dimethoxyamphetamine)

References

External links

Isomer Design
{{Chemical classes of psychoactive drugs 3C (psychedelics) Chemical classes of psychoactive drugs Psychedelic phenethylamines

List of 3C drugs

4-Methoxylated

Other 4-substituted

See also

References

External links