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Psychedelic drug
Pharmaceutical compound
F-2 , also known as 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran or as benzofuran-2-methyl-5-methoxy-6-(2-aminopropane) , is a chemical compound and possible psychedelic drug of the phenethylamine , amphetamine , and benzofuran families.[ 1] derivative of 6-APDB with a methyl group at the 2 position and a methoxy group at the 5 position of the benzofuran ring system .[ 1]
In his book PiHKAL Phenethylamines I Have Known and Loved ), Alexander Shulgin lists F-2's dose as greater than 15 mg orally and its duration as unknown.[ 1] mg.[ 1] [ 1] [ 1] David E. Nichols reported in 1981, via personal communication with Shulgin and M. Trampota in 1980, that F-2 was "shown to possess clinical activity".[ 2]
F-2 has been found to substitute for the psychedelic drug DOM in drug discrimination tests in rats.[ 1] [ 3] [ 4] potent than DOM in this regard, requiring a dose of 5 mg/kg.[ 1] mg/kg.[ 1] mg/kg intraperitoneally in mice was without effects.[ 1] mg/kg intraperitoneally in mice was lethal.[ 1]
The chemical synthesis of F-2 has been described.[ 1]
Analogues of F-2 include DOPR , 6-APDB , MMDA-2 , F (F-1), and F-22 , among others.[ 1]
F-2 was first described in the scientific literature by David E. Nichols in 1981 via personal communication with Alexander Shulgin and M. Trampota in 1980.[ 2] [ 3] [ 4] PiHKAL Phenethylamines I Have Known and Loved ) in 1991.[ 1] F and its derivatives in a paper in 1971.[ 5]
Society and culture [ edit ] This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act .[ 6]
^ 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 ISBN 0-9630096-0-5 OCLC 25627628 .F-2 Entry ^ a b Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences . 70 (8): 839– 849. Bibcode :1981JPhmS..70..839N . doi :10.1002/jps.2600700802 . PMID 7031221 . ^ a b Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). "Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats". Journal of Medicinal Chemistry . 29 (2): 302– 304. doi :10.1021/jm00152a022 . PMID 3950910 . ^ a b Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". J Med Chem . 34 (1): 276– 281. doi :10.1021/jm00105a043 . PMID 1992127 . ^ Shulgin AT (1971). "Preliminary studies of the synthesis of nitrogen analogs of Δ1-THC" . Acta Pharm Suecia . 8 : 680– 681. Archived from the original on 2025-07-12. A preliminary study to this end has been the synthesis of a number of benzofuran and benzopyren counterparts. The synthesis of several methyl substituted furan compounds of the general formula: [structure] have been completed and some chemical problems associated with these syntheses will be discussed. ^ "UK Misuse of Drugs act 2001 Amendment summary" . Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014 .
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 )O -MethylnordehydrobufoteninePartial 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 )
Benzofurans (e.g., 5-MeO-DiBF (1-oxa-5-MeO-DiPT) , dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) , mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) )Benzothiophenes (e.g., 3-APBT (1-thia-AMT) )Indazolethylamines (e.g., AL-38022A , O -methyl-AL-34662Indenylethylamines (e.g., C-DMT )Isotryptamines (e.g., 6-MeO-isoDMT , Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g., mefloquine )
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) BOB , BOD , BOHB )HOT-2 , HOT-7 , HOT-17 )N -Ethyl-2C-B2CB-2-EtO , 2CD-2-EtO , 2CD-5-EtO , 2CE-5-EtO , 2CE-5iPrO , 2CT2-2-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 )CT-5172 DMAs (e.g., 2,4-DMA , 3,4-DMA )Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine 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 )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 )Glaucine 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
Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP )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.Acacia acuminata Acacia confusa Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum 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.Periglandula ipomoeae Periglandula clandestina
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
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 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , bromotomscaline , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Camfetamine 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 Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )Pyridopyrroloquinoxalines (e.g., lumateperone , deulumateperone , IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )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 )
