F-22 (drug)

F-22
Clinical data
Other names	6-(2-Aminopropyl)-2,2-dimethyl-5-methoxy-2,3-dihydrobenzofuran; Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane); 2,2-DiMe-5-MeO-6-APDB
Routes of; administration	Oral
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 1-(5-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-yl)propan-2-amine;
CAS Number	952016-51-2 ;
PubChem CID	16051705;
ChemSpider	13180083 ;
UNII	QS9HMZ85HN;
CompTox Dashboard (EPA)	DTXSID50581591 ;
Chemical and physical data
Formula	C14H21NO2
Molar mass	235.327 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=C2C(=CC(=C1CC(C)N)OC)CC(O2)(C)C;
	InChI InChI=1S/C14H21NO2/c1-9(15)5-10-6-13-11(7-12(10)16-4)8-14(2,3)17-13/h6-7,9H,5,8,15H2,1-4H3 ; Key:ZUGGTXPIKSRFHP-UHFFFAOYSA-N ;
	(verify)

F-22, also known as 6-(2-aminopropyl)-2,2-dimethyl-5-methoxy-2,3-dihydrobenzofuran or as benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane), is a chemical compound of the phenethylamine, amphetamine, and benzofuran families.^[1]^[2]^[3] It is the derivative of 6-APDB with two methyl groups 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) and other publications, Alexander Shulgin lists F-22's dose as greater than 15 mg orally and its duration as unknown.^[1]^[2]^[3] The drug produced no effects at assessed doses of up to 15 mg.^[1]^[2]^[3] Higher doses were not tested.^[1]^[2] It is unknown whether F-22 is active.^[1]

Chemistry

Synthesis

The chemical synthesis of F-22 has been described.^[1]

Analogues

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

History

F-22 was first described in the scientific literature by Alexander Shulgin in 1978.^[2] Subsequently, it was described in greater detail 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.^[4]

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.^[5]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. F-22 Entry
^ ^a ^b ^c ^d ^e Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.4.12. 6-(2-Aminoporpyl)-2,2-dimethyl-5-methoxy-2,3-dihydrofuran In a synthetic study of 4-alkyl-substituted 2,5-dimethoxyphenylisopropylamines, a number of compounds were prepared in which the 4-alkyl and the 5-alkoxy groups were tied together in a furan or a pyran ring, thus showing a passing resemblance to the heterocyclic structure of tetrahydrocannabinol (Shulgin, 1971). The title compound (78) has been assayed as a psychotomimetic and is at least one order of magnitude less potent than the isosteric analogs DOET (74) and DOPR (75). There are no detectable effects noted following oral administration in excess of 10 mg, acutely.
^ ^a ^b ^c Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". J Pharm Sci. 70 (8): 839–849. doi:10.1002/jps.2600700802. PMID 7031221. Evidence to support the idea of a deleterious effect of bulky substituents comes from studies on two series of homologs. Structures XII, XIII, XV, and XVI were shown to possess clinical activity (36,51). Compound XIV has not been tested in humans, but was inactive in animal models (52). The gem-dimethyl compound (XVII) is inactive in humans (20). This pattern of activity is in agreement with the suggestion that one face of the molecule must remain unhindered. This explanation may apply to the inactivity of the ethylenedioxy (XVIIIa) and trimethylenedioxy (XVIIIb) compounds (53).
^ 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] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. F-22 Entry

[Shulgin1978-2] Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.4.12. 6-(2-Aminoporpyl)-2,2-dimethyl-5-methoxy-2,3-dihydrofuran In a synthetic study of 4-alkyl-substituted 2,5-dimethoxyphenylisopropylamines, a number of compounds were prepared in which the 4-alkyl and the 5-alkoxy groups were tied together in a furan or a pyran ring, thus showing a passing resemblance to the heterocyclic structure of tetrahydrocannabinol (Shulgin, 1971). The title compound (78) has been assayed as a psychotomimetic and is at least one order of magnitude less potent than the isosteric analogs DOET (74) and DOPR (75). There are no detectable effects noted following oral administration in excess of 10 mg, acutely.

[Nichols1981-3] Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". J Pharm Sci. 70 (8): 839–849. doi:10.1002/jps.2600700802. PMID 7031221. Evidence to support the idea of a deleterious effect of bulky substituents comes from studies on two series of homologs. Structures XII, XIII, XV, and XVI were shown to possess clinical activity (36,51). Compound XIV has not been tested in humans, but was inactive in animal models (52). The gem-dimethyl compound (XVII) is inactive in humans (20). This pattern of activity is in agreement with the suggestion that one face of the molecule must remain unhindered. This explanation may apply to the inactivity of the ethylenedioxy (XVIIIa) and trimethylenedioxy (XVIIIb) compounds (53).

[Shulgin1971-4] 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.

[5] "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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