F-2 (drug)

F-2
Clinical data
Other names	6-(2-Aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran; Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane); 2-Me-5-MeO-6-APDB
Routes of; administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	CA: Schedule I; UK: Class A;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 1-(5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)propan-2-amine;
CAS Number	99355-74-5 ;
PubChem CID	13056773;
ChemSpider	21106309 ;
UNII	75S5T5T7QX;
ChEMBL	ChEMBL102877 ;
Chemical and physical data
Formula	C13H19NO2
Molar mass	221.300 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=C2C(=CC(=C1CC(C)N)OC)CC(O2)C;
	InChI InChI=1S/C13H19NO2/c1-8(14)4-10-7-13-11(5-9(2)16-13)6-12(10)15-3/h6-9H,4-5,14H2,1-3H3 ; Key:XBHKBTCXRYPZMX-UHFFFAOYSA-N ;
	(verify)

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] It is the 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]

Use and effects

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] The drug produced no effects at assessed doses of up to 15 mg.^[1] Higher doses were not tested.^[1] It is unknown whether F-2 is active.^[1] On the other hand, 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]

Interactions

Pharmacology

Pharmacodynamics

F-2 has been found to substitute for the psychedelic drug DOM in drug discrimination tests in rats.^[1]^[3]^[4] However, it was about 40-fold less potent than DOM in this regard, requiring a dose of 5 mg/kg.^[1] For comparison, F-2 was tested in humans at doses of only up to 0.2 mg/kg.^[1] In contrast to the case of rats, F-2 at doses of up to 100 mg/kg intraperitoneally in mice was without effects.^[1] A dose of 150 mg/kg intraperitoneally in mice was lethal.^[1]

Chemistry

Synthesis

The chemical synthesis of F-2 has been described.^[1]

Analogues

Analogues of F-2 include DOPR, 6-APDB, MMDA-2, F (F-1), and F-22, among others.^[1]

History

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] Subsequently, it was described in greater detail by Nichols and colleagues in 1986^[3] and 1991^[4] and by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.^[1] Shulgin briefly alluded to F and its derivatives in a paper in 1971.^[5]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[6]

References

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. F-2 Entry
1 2 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.
1 2 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.
1 2 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.

External links

[PiHKAL-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. F-2 Entry

[Nichols1981-2] 1 2 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.

[NicholsHoffmanOberlender1986-3] 1 2 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.

[NicholsSnyderOberlender1991-4] 1 2 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.

[Shulgin1971-5] 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.

[6] "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.

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