2C-G

2C-G
Clinical data
Other names	2C-G-0; 2,5-Dimethoxy-3,4-dimethylphenethylamine; 3,4-Dimethyl-2,5-dimethoxyphenethylamine; 3-Methyl-2C-D
Routes of; administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	In general Unscheduled;
Pharmacokinetic data
Duration of action	18–30 hours
Identifiers
	IUPAC name 2-(2,5-dimethoxy-3,4-dimethylphenyl)ethan-1-amine;
CAS Number	207740-18-9 ;
PubChem CID	22238091;
ChemSpider	21106224 ;
UNII	DTG7FMO01J;
ChEMBL	ChEMBL127202 ;
CompTox Dashboard (EPA)	DTXSID70174848 ;
Chemical and physical data
Formula	C12H19NO2
Molar mass	209.289 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1c(C)c(C)c(cc1CCN)OC;
	InChI 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 ; Key:NFOHGLKGLZIHJQ-UHFFFAOYSA-N ;
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2C-G, or 2C-G-0, also known as 3,4-dimethyl-2,5-dimethoxyphenethylamine or as 3-methyl-2C-D, is a psychedelic phenethylamine of the 2C family.^[1] First synthesized by Alexander Shulgin, it has structural and pharmacodynamic properties similar to 2C-D and Ganesha (G).^[1] The drug has a number of known homologues, which are known as the 2C-G series of compounds.^[1]

Use and effects

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

Interactions

Chemistry

Synthesis

The chemical synthesis of 2C-G has been described.^[1]

Homologues

Several homologues of 2C-G (2C-G-0) were also synthesized and/or tested by Alexander Shulgin.^[1] These include 2C-G-3, 2C-G-5, and 2C-G-N.^[1] 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.^[1]

Compound	Details	Structure
2C-G-1	CAS #: 2888537-47-9 The synthesis of this compound has not been reported, but it is described prophetically in WO2022271982 DOx analogue: None
2C-G-2	CAS #: 2888537-48-0 The synthesis of this compound has not been reported, but it is described prophetically in WO2022271982 DOx analogue: None
2C-G-3	CAS #: 207740-19-0 Dose: 16–25 mg Duration: 12–24 hours Effects: Some visual effects. General euphoria with an underlying sense of paranoia. DOx analogue: G-3
2C-G-4	CAS #: 952006-59-6 Partially synthesized but not tested. DOx analogue: G-4
2C-G-5	CAS #: 207740-20-3 Dose: 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). DOx analogue: G-5
2C-G-6	CAS #: 2888537-49-1 The synthesis of this compound has not been reported, but it is described prophetically in WO2022271982 DOx analogue: None
2C-G-N	CAS #: 207740-21-4 Dose: 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. DOx analogue: G-N

History

2C-G was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Legal status

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 I controlled substance as a positional isomer of 2C-E and DOM.^[3]^[4]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Shulgin AT, Shulgin A (1991). "2C-G". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OL 22859055M.
^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
^ "Lists of: Scheduling Actions - Controlled Substances - Regulated Chemicals" (PDF). Drug Enforcement Administration. February 2023.
^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Shulgin AT, Shulgin A (1991). "2C-G". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OL 22859055M.

[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.

[DEA2007-4] Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.

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