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 mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

s containing methoxy groups at the 3 and 5 positions of the

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

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 struc ...

s are analogues of

3,4,5-trimethoxyamphetamine 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of ...

(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- positio ...

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 analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine). Other ...

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 is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

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 In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...

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

2C-O 2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a chemical compound of the phenethylamine and 2C families. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue o ...

(2,4,5-trimethoxyphenethylamine) drugs (e.g., 2C-O-4) and the 2,4,5-trimethoxyamphetamine (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'' 𐡌, Syriac ''mīm'' ܡ, Arabic ''mīm'' , and Phoenician ''mēm'' 𐤌. Its sound value is . It is also relate ...

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

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

and

Daniel Trachsel Daniel Trachsel is a Swiss people, Swiss chemist who studies psychedelic drug, psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen chemical compound, compounds, including their psycho ...

, among others. The

pharmacology Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur betwee ...

of 3C drugs has been studied and described.

List of 3C drugs

4-Methoxylated

3,4,5-Trimethoxyamphetamine 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of ...

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

3C-AL 3C-AL (4-Allyloxy-3,5-dimethoxyamphetamine) 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 synt ...

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

3C-BZ 3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as 3C-benzscaline, is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. Use and effects In Shulgin's book ''PiHKAL'', the ...

(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 (3,5-Dimethoxy-4-ethoxyamphetamine) 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 act ...

(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 (4-Methylallyloxy-3,5-dimethoxyamphetamine) 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. Th ...

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

3C-P 3C-P, also known as 4-propoxy-3,5-dimethoxyamphetamine, is a psychedelic phenethylamine. It has structural and pharmacodynamic properties similar to the drugs mescaline, proscaline, and amphetamine. Little information exists on the human pharma ...

(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-PhPr-3,5-DMA, also known as 4-(3-phenylpropyl)-3,5-dimethoxyamphetamine, is a serotonin receptor modulator of the phenethylamine and amphetamine families. It is structurally related to the DOx drugs but has one of its methoxy groups in the 3 ...

(4-(3-phenylpropyl)-3,5-dimethoxyamphetamine)

References

External links

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

List of 3C drugs

4-Methoxylated

Other 4-substituted

See also

References

External links