2C-G-5

2C-G-5, also known as 3,4-norbornyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.^[1][2][3][4] It is one of several homologues of 2C-G (3,4-dimethyl-2,5-dimethoxyphenethylamine).^[1][2][3][4] The drug is taken orally.^[1][2][3]

2C-G-5

Clinical data
Other names	3,4-Norbornyl-2,5-DMPEA; 3,4-Norbornyl-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-3,4-norbornylphenethylamine; 3,6-Dimethoxy-4-(2-aminoethyl)benzonorbornane
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Onset of action	1–2 hours[1]
Duration of action	32–48 hours[1]
Identifiers
IUPAC name 2-(3,6-dimethoxy-4-tricyclo[6.2.1.02,7]undeca-2,4,6-trienyl)ethanamine
CAS Number	207740-20-3
PubChem CID	44349968
ChemSpider	23206405
ChEMBL	ChEMBL123976
CompTox Dashboard (EPA)	DTXSID401016884
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.338 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C2C3CCC(C3)C2=C(C(=C1)CCN)OC
InChI InChI=1S/C15H21NO2/c1-17-12-8-11(5-6-16)15(18-2)14-10-4-3-9(7-10)13(12)14/h8-10H,3-7,16H2,1-2H3 Key:ASPWVWSIJQTXDB-UHFFFAOYSA-N

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2C-G-5's dose as 10 to 16 mg orally and its duration as 32 to 48 hours.^[1][2][3] The drug's onset is 1 to 2 hours and its time to peak is 2.5 to 3 hours.^[1] 2C-G-5 is reported to produce psychedelic effects including visuals, clear and cosmic thinking, and 2C-B-like enhanced eroticism, among others.^[1] It is among the most potent of the 2C psychedelics.^[1][2][3] However, its duration is described as too long, interfering with sleep and resulting in subsequent-day consequences like tiredness and sleepiness.^[1] 2C-G-5 was also the longest-lasting drug included in PiHKAL based on its specified duration.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Chemistry

Synthesis

The chemical synthesis of 2C-G-5 has been described.^[1]

Analogues

Analogues of 2C-G-5 include other compounds of the 2C-G and Ganesha series, among others.^[1]

History

2C-G-5 was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1][2][3][4]

See also

• 2C (psychedelics)
• 2C-G (2C-G-0)
• 2C-G-3 and 2C-G-N
• Ganesha and G-5