2C-G-5

Last updated

2C-G-5
2C-G-5.svg
2C-G-5 ball-and-stick structure.png
Clinical data
Other names3,4-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] [2]
Duration of action 32–48 hours [1] [2]
Identifiers
  • 2-(3,6-dimethoxy-4-tricyclo[6.2.1.02,7]undeca-2,4,6-trienyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H21NO2
Molar mass 247.338 g·mol−1
3D model (JSmol)
  • COC1=C2C3CCC(C3)C2=C(C(=C1)CCN)OC
  • 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]

Contents

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

Canada

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

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 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".
  2. 1 2 3 4 5 6 7 8 9 10 11 "2C-G-5". АИПСИН (in Russian). Retrieved 1 January 2026.
  3. 1 2 3 4 5 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)). [...]
  4. 1 2 3 4 5 6 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.
  5. 1 2 3 4 5 6 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.
  6. 1 2 3 4 5 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.
  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 [...]
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