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This article is about the psychedelic drug. For other uses, see
G5 .
Pharmaceutical compound
G-5 Other names G5; Ganesha-5; GANESHA-5; 3C-G-5; 3,4-Norbornyl-2,5-dimethoxyamphetamine; 3,6-Dimethoxy-4-(2-aminopropyl)benzonorbornane; DOG-5 Routes of administration Oral [ 1] Drug class Serotonergic psychedelic ; Hallucinogen ATC code Onset of action Very slow[ 1] Duration of action 16–30 hours[ 1]
1-(3,6-dimethoxy-4-tricyclo[6.2.1.02,7 ]undeca-2,4,6-trienyl)propan-2-amine
CAS Number PubChem CID ChemSpider Formula C 16 H 23 N O 2 Molar mass 261.365 g·mol−1 3D model (JSmol )
CC(CC1=CC(=C2C3CCC(C3)C2=C1OC)OC)N
InChI=1S/C16H23NO2/c1-9(17)6-12-8-13(18-2)14-10-4-5-11(7-10)15(14)16(12)19-3/h8-11H,4-7,17H2,1-3H3
Key:MZFVFTFFHRCTIO-UHFFFAOYSA-N
G-5 , also known as 3,4-norbornyl-2,5-dimethoxyamphetamine , is a psychedelic drug of the phenethylamine , amphetamine , and DOx families.[ 1] [ 2] [ 3] It is one of several homologues of Ganesha (G).[ 1] [ 2] [ 3]
In his book PiHKAL (Phenethylamines I Have Known and Loved ) and other publications, Alexander Shulgin lists G-5's dose as 14 to 20 mg orally and its duration as 16 to 30 hours.[ 1] [ 2] [ 3] It is said to have a very slow onset .[ 1] The effects of G-5 were reported to include an unexpected absence of visual and related sensory activity, excellent mental activity, "absence of the bells and whistles that are expected with a psychedelic in full bloom", mental integration, and little or no body load .[ 1] According to Shulgin, it was somehow lacking in characteristics that would have made it fully favorable, perhaps the lack of perceptual effects, which resulted in there being little drive to further explore it.[ 1]
G-5 is not a monoamine releasing agent of either serotonin or dopamine .[ 4]
The chemical synthesis of G-5 has been described.[ 1]
G-5 was first described in the literature by Alexander Shulgin and colleagues in 1991.[ 1] [ 4] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved ) that same year.[ 1]
Society and culture [ edit ]
G-5 is a controlled substance in Canada under phenethylamine blanket-ban language.[ 5]
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others
Ergolines /lysergamides (e.g., LSD )
Ibogalogs (e.g., ibogainalog , tabernanthalog , Pharm-136 )
O -Methylnordehydrobufotenine
Partial ergolines (e.g., NDTDI , RU-28306 , CT-5252 )
Piperidinylethylindoles (e.g., pip-T )
Pyrrolidinylethylindoles (e.g., pyr-T , 5-MeO-pyr-T )
Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5-MeO-MPMI , MSP-2020 )
Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI) , NEtPhOH-THPI )
Others: 2C-B-AN
2C-DB
2C-G-x (e.g., 2C-G-3 , 2C-G-5 )
β-Keto-2C-B (βk-2C-B)
β-Keto-2C-I (βk-2C-I)
β-Methyl-2C-B (BMB)
(e.g., BOB , BOD , BOHB )
(e.g., HOT-2 , HOT-7 , HOT-17 )
N -Ethyl-2C-B
(e.g., 2CB-2-EtO , 2CD-2-EtO , 2CD-5-EtO , 2CE-5-EtO , 2CE-5iPrO , 2CT-5-EtO , 2CT2-2-EtO , 2CT7-2-EtO , ASR-2001 (2CB-5-PrO) )
Others
25B-NAcPip
2-DM-DOM
4-HA
5-DM-DOM
Benzofurans (e.g., 5-APB , 5-APDB , 6-APB , 6-APDB , F , F-2 , F-22 )
Benzothiophenes (e.g., 5-APBT , 6-APBT )
BMB-202
CT-5172
DMAs (e.g., 2,4-DMA , 3,4-DMA )
Fenfluramine
MMA (3-MeO-4-MA)
Norfenfluramine
(e.g., 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )
PMA (4-MA)
Thio-2Cs (e.g., 2C-5-TOET )
Thio-DOx (e.g., 2-TOM , 5-TOET , 5-TOM , TOMSO )
(e.g., TMA-3 , TMA-4 , TMA-5 )
ZDCM-04 (DOC-fenethylline)
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )
2-Aminoindanes (e.g., DOM-AI )
3-Benzazepines (e.g., lorcaserin )
3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )
Benzocyclobutenes (e.g., 2CBCB-NBOMe , TCB-2 , tomscaline )
Benzoxepins (e.g., BBOX , IBOX , TFMBOX )
DMBMPP (juncosamine)
Ergolines /lysergamides (e.g., LSD )
Partial ergolines (e.g., NDTDI , DEIMDHPCA , DEMPDHPCA , DEMTMPDHPCA , DEMNDHPCA )
Phenylcyclopropylamines (e.g., DMCPA , TMT )
Phenyloxazolamines (aminorexes ) (e.g., 2C-B-aminorex )
Pyridopyrroloquinoxalines (e.g., IHCH-7113 )
Z3517967757
ZC-B
Others
9-Oxaergolines (e.g., RU-29717 )
γ-Carbolines (e.g., tiflucarbine )
Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP , VCU-1012 )
Dihydrobenzoxazines (e.g., efavirenz )
Phenoxyethylamines (e.g., CT-4719 , ORG-37684 )
Pyridopyrroloquinoxalines (e.g., IHCH-7113 )
Quinazolinylethylamines (e.g., RH-34 )
Natural sources
Tryptamines: Acacia spp. (e.g., Acacia acuminata , Acacia confusa )
Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna) , Dipolopterys cabrerana (chaliponga, chacruna) , Mimosa tenuiflora (Mimosa hostilis ; jurema) )
Brosimum (e.g., Brosimum acutifolium (takini) )
Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene) , Anadenanthera colubrina (vilca, cebil) )
Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)
Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis , Psilocybe mexicana (teonanacatl) )
Lysergamides: Achnatherum robustum (sleepy grass)
Epichloë spp.
Ergot (Claviceps ) (e.g., Claviceps purpurea , Claviceps paspali )
Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea ) , Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa ) , Argyreia nervosa (Hawaiian baby woodrose; HBWR) )
Periglandula spp. (e.g., Periglandula ipomoeae , Periglandula clandestina )
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized phenethylamines
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , bromojimscaline , jimscaline )
2-ADN
2-Benzhydrylpyrrolidine
2C-B-5-hemiFLY-α6 (BNAP)
2C-B-PYR
2CBecca
2CB7
2CJP
2CLisaB
2CLisaH
3-Aminochromans (e.g., CT-5126 , 5-MeO-DPAC , robalzotan , ebalzotan )
3-Benzazepines (e.g., fenoldopam , lorcaserin , 7-chlorolorcaserin , SCHEMBL5334361 )
3-Benzhydrylmorpholine
3-Phenylpiperidines (e.g., 3-phenylpiperidine , 3-PPP , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 , 2C-B-3PIP , 2C-B-3PIP-NBOMe , 2C-B-3PIP-POMe , Z3517967757 (Z7757) )
6-AB
AL-1095
Aminochromes (e.g., adrenochrome , adrenolutin )
AMMT
Benzocyclobutenes (e.g., 2CBCB-NBOMe , bromotomscaline , S33005 , TCB-2 , tomscaline )
Benzoxepins (e.g., BBOX , IBOX , TFMBOX )
Butyltolylquinuclidine
Camfetamine
Clausenamide
Cypenamine (trans -2-phenylcyclopentylamine)
Diphenidine
Diphenylprolinol
Ergolines (e.g., LSD )
Fencamfamin
GYKI-52895
HDMP-29
Ivabradine
Methoxphenidine
Methylmorphenate
Milnacipran
MT-45
2-Naphthylamine
Org 6582
Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , DEMPDHPCA-2C-D , RU-27251 )
PF-592,379
Phenanthrenes (e.g., atherosperminine (atherospermine) )
Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )
Phenylmethylpyrrolidines (e.g., APA-01 )
Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )
Pyridopyrroloquinoxalines (e.g., lumateperone , deulumateperone , IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )
Thienopyridines (e.g., SKF-89145 , SKF-89615 , SKF-89626 )
Tolazoline
Tricyclics (e.g., AMDA , AMDH , benzoctamine , dizocilpine , SpAMDA )
ZC-B
Related compounds
2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )
Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )
Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )
Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )
Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )
Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )
Phenylalkenylamines (e.g., phenylbutenamine )
Phenylalkynylamines (e.g., phenylbutynamine )
Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )
Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )
Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
Phenylbutylamines (e.g., 4-Phenylbutylamine , 4-Phenylpentan-1-amine )