G-130

G-130
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 2-phenyl-5,5-dimethylmorpholine;
CAS Number	42013-48-9 ;
PubChem CID	97711;
ChemSpider	88190;
UNII	785F2C727T;
CompTox Dashboard (EPA)	DTXSID401032153 DTXSID40963342, DTXSID401032153 ;
Chemical and physical data
Formula	C12H17NO
Molar mass	191.274 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(C)NCC(OC1)C2=CC=CC=C2;
	InChI InChI=1S/C12H17NO/c1-12(2)9-14-11(8-13-12)10-6-4-3-5-7-10/h3-7,11,13H,8-9H2,1-2H3; Key:KJUOROGOOZJYAI-UHFFFAOYSA-N;
	(verify)

G-130 (GP-130, 2-Phenyl-5,5-dimethyltetrahydro-1,4-oxazine)^[1] is a drug with stimulant and anorectic effects, related to phenmetrazine.^[2]^[3]^[4]

Structural analogs

Compounds related to G-130 and radafaxine were synthesized that behave as combined inhibitors of monoamine uptake and nicotinic acetylcholine receptors.^[5]

Synthesis

Patent:^[1] Spanish Fepradinol patent:^[6]

Ex 1: 2 moles of 2-methyl-2-aminopropanol (aminomethyl propanol) (1) is reacted with 1 moles of styrene oxide (phenyloxirane) [96-09-3] (2) in 0.2 mole water.

Ex 2: Fepradinol [36981-91-6] [63075-47-8] (3) is treated with acid, to cyclize to the morpholine ring.

References

^ ^a ^b GB 1336732, "Diethanolamine derivatives", published 1973-11-07, assigned to Instituto Gentili SPA
^ Fanelli O (June 1973). "Pharmacological and toxicological study of a new psychotropic stimulant: the 2-phenyl-5-dimethyl-tetrahydro-1,4-oxazine, in comparison with d,l-amphetamine, phenmetrazine and pemoline-Mg". Arzneimittel-Forschung. 23 (6): 810–816. PMID 4740767.
^ Fanelli O, Mazzoncini V, Ferri S (October 1974). "Toxicological and teratological study of 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130), a psychostimulant drug". Arzneimittel-Forschung. 24 (10): 1627–1632. PMID 4479774.
^ Fanelli O, Mazzoncini V, Trallori L (December 1974). "Antagonism of psychostimulant 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130) to central nervous system depressing drugs. Monoamine oxidase inhibitory activity and norepinephrine and serotonin induced changes. Comparison with dL-amphetamine". Arzneimittel-Forschung. 24 (12): 2025–2029. PMID 4480283.
^ Carroll FI, Muresan AZ, Blough BE, Navarro HA, Mascarella SW, Eaton JB, et al. (March 2011). "Synthesis of 2-(substituted phenyl)-3,5,5-trimethylmorpholine analogues and their effects on monoamine uptake, nicotinic acetylcholine receptor function, and behavioral effects of nicotine". Journal of Medicinal Chemistry. 54 (5): 1441–1448. doi:10.1021/jm1014555. PMC 3048909. PMID 21319801.
^ ES508287 (application number) idem ES 8300676 (1983 to Elmu Sa).

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[patent-1] GB 1336732, "Diethanolamine derivatives", published 1973-11-07, assigned to Instituto Gentili SPA

[pmid4740767-2] Fanelli O (June 1973). "Pharmacological and toxicological study of a new psychotropic stimulant: the 2-phenyl-5-dimethyl-tetrahydro-1,4-oxazine, in comparison with d,l-amphetamine, phenmetrazine and pemoline-Mg". Arzneimittel-Forschung. 23 (6): 810–816. PMID 4740767.

[pmid4479774-3] Fanelli O, Mazzoncini V, Ferri S (October 1974). "Toxicological and teratological study of 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130), a psychostimulant drug". Arzneimittel-Forschung. 24 (10): 1627–1632. PMID 4479774.

[pmid4480283-4] Fanelli O, Mazzoncini V, Trallori L (December 1974). "Antagonism of psychostimulant 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130) to central nervous system depressing drugs. Monoamine oxidase inhibitory activity and norepinephrine and serotonin induced changes. Comparison with dL-amphetamine". Arzneimittel-Forschung. 24 (12): 2025–2029. PMID 4480283.

[5] Carroll FI, Muresan AZ, Blough BE, Navarro HA, Mascarella SW, Eaton JB, et al. (March 2011). "Synthesis of 2-(substituted phenyl)-3,5,5-trimethylmorpholine analogues and their effects on monoamine uptake, nicotinic acetylcholine receptor function, and behavioral effects of nicotine". Journal of Medicinal Chemistry. 54 (5): 1441–1448. doi:10.1021/jm1014555. PMC 3048909. PMID 21319801.

[6] ES508287 (application number) idem ES 8300676 (1983 to Elmu Sa).

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G-130

Contents

Structural analogs

Synthesis

See also

References