2C-G

Last updated
2C-G
2C-G-Chemdraw.png
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2C-G animation.gif
Names
Preferred IUPAC name
2-(2,5-Dimethoxy-3,4-dimethylphenyl)ethan-1-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H19NO2/c1-8-9(2)12(15-4)10(5-6-13)7-11(8)14-3/h7H,5-6,13H2,1-4H3 Yes check.svgY
    Key: NFOHGLKGLZIHJQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H19NO2/c1-8-9(2)12(15-4)10(5-6-13)7-11(8)14-3/h7H,5-6,13H2,1-4H3
    Key: NFOHGLKGLZIHJQ-UHFFFAOYAX
  • COc1c(C)c(C)c(cc1CCN)OC
Properties
C12H19NO2
Molar mass 209.289 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

2C-G is a psychedelic phenethylamine of the 2C-series. First synthesized by Alexander Shulgin, [1] it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in PiHKAL , 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects.

Contents

Chemistry

2C-G is 3,4-dimethyl-2,5-dimethoxyphenethylamine, with the formula C
12
H
19
N O
2
.

Dosage and effects

In Shulgin's book PiHKAL, the dosage range is listed as 20 to 35 mg. [1] Effects are similar to the related Ganesha, and are extremely long lasting; the duration is 18–30 hours. Visual effects are muted or absent, and it is described in PiHKAL as an "insight-enhancer". [1] Unlike other members of the 2C-series, 2C-G is nearly as potent as its amphetamine form.

Homologs

Several homologs of 2C-G were also synthesized by Shulgin. These include 2C-G-3, 2C-G-5, and 2C-G-N. Some, such as 2C-G-1, 2C-G-2, 2C-G-4, and 2C-G-6 are possible to synthesize in principle but impossible or extraordinarily difficult to do so in practice.

2C-G-1CAS: 2888537-47-9

The synthesis of this compound has not been reported, but it is described prophetically in WO2022271982

2C-G-1 2C-G-1.png
2C-G-1
2C-G-2CAS: 2888537-48-0

The synthesis of this compound has not been reported, but it is described prophetically in WO2022271982

2C-G-2 2C-G-2.png
2C-G-2
2C-G-3CAS: 207740-19-0

Dosage: 16–25 mg
Duration: 12–24 hours
Effects: Some visual effects. General euphoria with an underlying sense of paranoia.

2C-G-3 2C-G-3-Chemdraw.png
2C-G-3
2C-G-4CAS: 952006-59-6

Synthesized but not tested.

2C-G-4 2C-G-4.png
2C-G-4
2C-G-5CAS: 207740-20-3

Dosage: 10–16 mg
Duration: 32–48 hours
Effects: Similar to 2C-B for some users. General euphoria (sometimes followed by irritability), often leading to tiredness (likely due to duration).

2C-G-5 2C-G-5.svg
2C-G-5
2C-G-6CAS: 2888537-49-1

The synthesis of this compound has not been reported, but it is described prophetically in WO2022271982

2C-G-6 2C-G-6.png
2C-G-6
2C-G-NCAS: 207740-21-4

Dosage: 20–40 mg
Duration: 20–30 hours
Effects: Stimulation similar to that caused by amphetamines. General sense of unease or unfriendliness for most. 2C-G-N is sometimes called 2C-NPH due to the Naphthalene portion of the molecule.

2C-G-N 2C-G-N-Chemdraw.png
2C-G-N

Canada

As of October 31, 2016; 2C-G is a controlled substance (Schedule III) in Canada. [2]

United Kingdom

2C-G and all other compounds featuring in PiHKAL are Class A drugs in the United Kingdom.

United States

In the United States 2C-G is considered a Schedule 1 controlled substance as a positional isomer of 2C-E and 2,5-Dimethoxy-4-methylamphetamine (DOM). [3]

See also

Related Research Articles

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

<span class="mw-page-title-main">2C-I</span> Chemical compound

2C-I (2,5-Dimethoxy-4-iodophenethylamine) is a phenethylamine of the 2C family with psychedelic properties. It was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL. The drug has been used recreationally as psychedelic and other reported effects and was sometimes confused with the more potent chemical cousin 25I-NBOMe, nicknamed "Smiles," in the media.

<span class="mw-page-title-main">2C-E</span> Chemical compound

2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and documented in his book PiHKAL. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.

<span class="mw-page-title-main">2C-C</span> Chemical compound

2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated. 2C-C is schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July, 2012 under the Food and Drug Administration Safety and Innovation Act.

<span class="mw-page-title-main">2C-D</span> Chemical compound

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. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.

<span class="mw-page-title-main">2C-T-8</span> Chemical compound

2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.

<span class="mw-page-title-main">2C-N</span> Chemical compound

2C-N (2,5-dimethoxy-4-nitrophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2C-T-4</span> Chemical compound

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

<span class="mw-page-title-main">2C-T-19</span> Chemical compound

2C-T-19 (2,5-dimethoxy-4-butylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2C-T</span> Chemical compound

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.

<span class="mw-page-title-main">2C-O-4</span> Chemical compound

2C-O-4 (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. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethylamphetamine</span> Psychedelic drug

2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

<span class="mw-page-title-main">2C-F</span> Chemical compound

2C-F (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. 2C-F may be found as a brownish freebase oil, or as a white crystalline hydrochloride salt.

Ganesha (2,5-dimethoxy-3,4-dimethylamphetamine) is a lesser-known psychedelic drug. It is also a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 24–32 mg. The drug is usually taken orally, although other routes such as rectally may also be used. Ganesha is synthesized from 2,5-dimethoxy-3,4-dimethylbenzaldehyde. Ganesha is the amphetamine analog of 2C-G. It is a particularly long lasting drug, with the duration listed in PiHKAL as being 18–24 hours, which might make it undesirable to some users. It is named after the Hindu deity, Ganesha. Very little is known about the dangers or toxicity of ganesha. Effects of ganesha include:

<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.

<span class="mw-page-title-main">2C-T-13</span> Chemical compound

2C-T-13 is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL.

<span class="mw-page-title-main">2C-T-15</span> Chemical compound

2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

<span class="mw-page-title-main">2C-T-17</span> Chemical compound

2C-T-17 or 2,5-dimethoxy-4-(β-secbutylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

<span class="mw-page-title-main">2C-H</span> Chemical compound

2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.

Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL. Little is known about their dangers or toxicity.

References

  1. 1 2 3 PiHKAL entry on 2C-G
  2. "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  3. "Lists of: Scheduling Actions - Controlled Substances - Regulated Chemicals" (PDF). Drug Enforcement Administration. February 2023.