2C is a general name for the family of psychedelic

Psychedelic

The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...

 phenethylamine

Phenethylamine

Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...

s containing methoxy groups

Methoxy

In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...

 on the 2 and 5 positions

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 of the benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 ring. Most of these compounds also carry lipophilic

Lipophilic

Lipophilicity, , refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. These non-polar solvents are themselves lipophilic — the axiom that like dissolves like generally holds true...

 substituents at the 4 position, usually resulting in more potent and more metabolically

Metabolism

Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...

 stable and longer acting compounds. Most of the currently known 2C compounds were first synthesized by Alexander Shulgin

Alexander Shulgin

Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...

 in the 1970s and 1980s, and published in his book, PiHKAL

PiHKAL

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...

(Phenethylamines i Have Known And Loved). Dr. Shulgin also invented the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.

Nomenclature	R3	R4	2D Structure	3D Structure
2C-B 2C-B 2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...	H Hydrogen Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...	Br Bromine Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...
2C-C 2C-C 2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. The full name of the chemical is 2,5-dimethoxy-4-chlorophenethylamine. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally,...	H	Cl Chlorine Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...
2C-D 2C-D 2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. The full name of the chemical is...	H	CH3 Methyl group Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
2C-E 2C-E 2C-E is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is typically found as a white crystalline powder....	H	CH2CH3 Ethyl group In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....
2C-F 2C-F 2C-F, or 4-fluoro-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 250 mg...	H	F Fluorine Fluorine is the chemical element with atomic number 9, represented by the symbol F. It is the lightest element of the halogen column of the periodic table and has a single stable isotope, fluorine-19. At standard pressure and temperature, fluorine is a pale yellow gas composed of diatomic...
2C-G 2C-G 2C-G is a psychedelic phenethylamine of the 2C family. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha...	CH3	CH3
2C-G-3	(CH2)3
2C-G-4	(CH2)4
2C-G-N	(CH)4
2C-H 2C-H 2C-H, or 2,5-dimethoxyphenethylamine, is a lesser-known chemical of the 2C family. 2C-H was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage and duration are both unknown...	H	H
2C-I 2C-I 2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. It was described in Shulgin’s book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects...	H	I Iodine Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....
2C-N 2C-N 2C-N, or 2,5-Dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.-Chemistry:The full name of the chemical is 2-ethanamine....	H	NO2 Nitro compound Nitro compounds are organic compounds that contain one or more nitro functional groups . They are often highly explosive, especially when the compound contains more than one nitro group and is impure. The nitro group is one of the most common explosophores used globally...
2C-O 2C-O 2C-O or 2,4,5-Trimethoxyphenethylamine is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline and is structurally similar to the drug 2C-D.-Chemistry:...	H	OCH3 Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...
2C-O-4 2C-O-4 2C-O-4 or 4-isopropoxy-2,5-dimethoxyphenethylamine is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic, psychedelic, and entheogenic effects...	H	OCH(CH3)2 Alkoxy group In chemistry, the alkoxy group is an alkyl group singular bonded to oxygen thus: R—O. The range of alkoxy groups is great, the simplest being methoxy . An ethoxy group is found in the organic compound phenetol, C6H5OCH2CH3 which is also known as ethoxy benzene...
2C-P 2C-P 2C-P is a psychedelic phenethylamine and 2C compound first synthesized by Alexander Shulgin.-Chemistry:2C-P is 2,5-dimethoxy-4--propylphenethylamine. The full name of the chemical is 2-ethanamine.-Dosage:...	H	CH2CH2CH3 Propyl In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. It is the substituent form of the alkane propane...
2C-SE 2C-SE 2C-SE, or 2,5-methoxy-4-methylseleneophenethylamine, is a lesser-known psychedelic drug of the 2C family. It is the only phenethylamine that contains Selenium. It is also the 4-seleneo analogue of 2C-T. 2C-SE was first synthesized by Alexander Shulgin...	H	Se Selenium Selenium is a chemical element with atomic number 34, chemical symbol Se, and an atomic mass of 78.96. It is a nonmetal, whose properties are intermediate between those of adjacent chalcogen elements sulfur and tellurium... CH3
2C-T 2C-T 2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2....	H	SCH3 Thioether A thioether is a functional group in organosulfur chemistry with the connectivity C-S-C as shown on right. Like many other sulfur-containing compounds, volatile thioethers have foul odors. A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen...
2C-T-2 2C-T-2 2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...	H	SCH2CH3
2C-T-4 2C-T-4 2C-T-4 or 2,5-dimethoxy-4-isopropylthiophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:...	H	SCH(CH3)2
2C-T-7 2C-T-7 2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...	H	S(CH2)2CH3
2C-T-8 2C-T-8 2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:The full name of the chemical is 2,5-dimethoxy-4-cyclopropylmethylthiophenethylamine...	H	SCH2CH(CH2)2
2C-T-9 2C-T-9 2C-T-9 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:2C-T-9 is 2,5-dimethoxy-4--butylthiophenethylamine....	H	SC(CH3)3
2C-T-13 2C-T-13 2C-T-13 or 2,5-dimethoxy-4-phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL ....	H	S(CH2)2OCH3
2C-T-15 2C-T-15 2C-T-15 or 2,5-dimethoxy-4-phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL ....	H	SCH(CH2)2
2C-T-17 2C-T-17 2C-T-17 or 2,5-dimethoxy-4-phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL ....	H	SCH(CH3)CH2CH3
2C-T-21 2C-T-21 2C-T-21 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. It was the first psychedelic drug known to contain six different chemical elements in the structure.-Chemistry:...	H	S(CH2)2F
2C-TFM 2C-TFM 2C-TFM is a psychedelic phenethylamine of the 2C family. It was first synthesized in the laboratory of David E. Nichols. It has also been called 2C-CF3, a name derived from the para-trifluoromethyl group it contains.-Chemistry:...	H	CF3 Trifluoromethyl Trifluoromethyl is a functional group in organofluorines that has the formula -CF3. The naming of is group is derived from the methyl group , by replacing each hydrogen atom by a fluorine atom. The trifluomethyl group has a significant electronegativity that is often described as being...

External links

• Book II of PiHKAL.