2C-G-5

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
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Onset of action	1–2 hours
Duration of action	32–48 hours
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;
UNII	BW3Q32DFC9;
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;

2C-G-5, also known as 3,4-norbornyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.^[3]^[1]^[4]^[5]^[6]^[2] It is one of several homologues of 2C-G (3,4-dimethyl-2,5-dimethoxyphenethylamine).^[1]^[4]^[5]^[6] The drug is taken orally.^[1]^[4]^[5] 2C-G-5 was encountered online as a novel designer drug in 2025.^[2]

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.^[3]^[1]^[4]^[5]^[2] The drug's onset is 1 to 2 hours and its time to peak is 2.5 to 3 hours.^[1]^[2] 2C-G-5 is reported to produce psychedelic effects including visuals, clear and cosmic thinking, and 2C-B-like enhanced eroticism, among others.^[1]^[2] It is among the most potent of the 2C psychedelics.^[1]^[4]^[5] However, its duration is described as too long, interfering with sleep and resulting in subsequent-day consequences like tiredness and sleepiness.^[1]^[2] 2C-G-5 was also the longest-lasting drug included in PiHKAL based on its specified duration.^[3]^[1]

Interactions

Pharmacology

Data on the pharmacology and toxicology of 2C-G-5 are unavailable.^[2]

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.^[3]^[1]^[6] Examples include 2C-G (2C-G-0), 2C-G-3, 2C-G-4, 2C-G-N, and G-5.^[3]^[1]^[6]

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]^[4]^[5]^[6]^[2] It was encountered online as a novel designer drug in 2025.^[2]

Society and culture

Legal status

Canada

2C-G-5 is a controlled substance in Canada under phenethylamine blanket-ban language.^[7]

United States

2C-G-5 is not an explicitly controlled substance in the United States.^[8] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "2C-G-5".
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "2C-G-5". АИПСИН (in Russian). Retrieved 1 January 2026.
^ ^a ^b ^c ^d ^e Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 900–903. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025. Weitere 2C-G Derivate wurden von Shulgin untersucht, namentlich 2C-G-3 (8), 2C-G-4 (9. bis anhin nur synthetisch beschrieben), 2C-G-5 (10; zwei abhängige Stereozentren; Racemat) und 2C-G-N (11) [4]. Sie sind allesamt potente, psychedelisch wirksame Phenethylamine und wirken ebenfalls bemerkenswert lange; mit 2C-G-5 (10) liegt die vielleicht am längsten wirksame Verbindung der Phenylalkylamine überhaupt vor (32—48h)). [...]
^ ^a ^b ^c ^d ^e ^f Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Research Monograph. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.
^ ^a ^b ^c ^d ^e ^f Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
^ ^a ^b ^c ^d ^e Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026. 2C-phenethylamines and their salts, derivatives, isomers and salts of derivatives and isomers that correspond to the following chemical description : any substance that has a 1-amino-2-phenylethane structure substituted at the 2' and 5' or 2' and 6' positions of the benzene ring by an alkoxy or haloalkoxy group, or substituted at two adjacent carbon atoms of the benzene ring which results in the formation of a furan, dihydrofuran, pyran, dihydropyran or methylenedioxy group — whether or not further substituted on the benzene ring to any extent, whether or not substituted at the amino group by one or two, or a combination of, methyl, ethyl, propyl, isopropyl, hydroxyl, benzyl (or benzyl substituted to any extent) or benzylene (or benzylene substituted to any extent) groups and whether or not substituted at the 2-ethyl (beta carbon) position by a hydroxyl, oxo or alkoxy group — and its salts and derivatives and salts of derivatives, including [...]
^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "2C-G-5".

[Aipsin-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "2C-G-5". АИПСИН (in Russian). Retrieved 1 January 2026.

[TrachselLehmannEnzensperger2013-3] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 900–903. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025. Weitere 2C-G Derivate wurden von Shulgin untersucht, namentlich 2C-G-3 (8), 2C-G-4 (9. bis anhin nur synthetisch beschrieben), 2C-G-5 (10; zwei abhängige Stereozentren; Racemat) und 2C-G-N (11) [4]. Sie sind allesamt potente, psychedelisch wirksame Phenethylamine und wirken ebenfalls bemerkenswert lange; mit 2C-G-5 (10) liegt die vielleicht am längsten wirksame Verbindung der Phenylalkylamine überhaupt vor (32—48h)). [...]

[Jacob_1994-4] ^ ^a ^b ^c ^d ^e ^f Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Research Monograph. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.

[Shulgin_2003-5] ^ ^a ^b ^c ^d ^e ^f Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.

[Shulgin_2011-6] Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.

[CDSA-7] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026. 2C-phenethylamines and their salts, derivatives, isomers and salts of derivatives and isomers that correspond to the following chemical description : any substance that has a 1-amino-2-phenylethane structure substituted at the 2' and 5' or 2' and 6' positions of the benzene ring by an alkoxy or haloalkoxy group, or substituted at two adjacent carbon atoms of the benzene ring which results in the formation of a furan, dihydrofuran, pyran, dihydropyran or methylenedioxy group — whether or not further substituted on the benzene ring to any extent, whether or not substituted at the amino group by one or two, or a combination of, methyl, ethyl, propyl, isopropyl, hydroxyl, benzyl (or benzyl substituted to any extent) or benzylene (or benzylene substituted to any extent) groups and whether or not substituted at the 2-ethyl (beta carbon) position by a hydroxyl, oxo or alkoxy group — and its salts and derivatives and salts of derivatives, including [...]

[OrangeBook2026-8] Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

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