Methoxyphenamine

Methoxyphenamine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	R03CB02 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 1-(2-methoxyphenyl)-N-methylpropan-2-amine;
CAS Number	93-30-1;
PubChem CID	4117;
ChemSpider	3974;
UNII	J3Z5SRI26Z;
CompTox Dashboard (EPA)	DTXSID0023292 ;
ECHA InfoCard	100.002.035
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC=CC=C1OC)NC;
	InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-6-4-5-7-11(10)13-3/h4-7,9,12H,8H2,1-3H3; Key:OEHAYUOVELTAPG-UHFFFAOYSA-N;

Methoxyphenamine (trade names ASMI, Euspirol, Orthoxine, Ortodrinex, Proasma), also known as 2-methoxy-N-methyl amphetamine (OMMA), is a β-adrenergic receptor agonist of the amphetamine class used as a bronchodilator.^[1]

It acts as an anti-inflammatory in rats.^[2]

Chemistry

Methoxyphenamine was first synthesized at the Upjohn company by Woodruff and co-workers.^[3] A later synthesis by Heinzelman, from the same company, corrects the melting point given for methoxyphenamine hydrochloride in the earlier paper, and describes an improved synthetic procedure, as well as resolution of the racemic methoxyphenamine.^[4]

References

^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
^ Wang YH, Bai CX, Hong QY, Chen J (December 2003). "Anti-inflammatory effect of methoxyphenamine compound in rat model of chronic obstructive pulmonary disease". Acta Pharmacologica Sinica. 24 (12): 1324–7. PMID 14653967.
^ Woodruff EH, Lambooy JP, Burt WE (April 1940). "Physiologically active amines. III. Secondary and tertiary β-phenylpropylamines and β-phenylisopropylamines". Journal of the American Chemical Society. 62 (4): 922–4. doi:10.1021/ja01861a060.
^ Heinzelman RV (February 1953). "Physiologically active secondary amines. β-(o-Methoxyphenyl)-isopropyl-N-methylamine and related compounds". Journal of the American Chemical Society. 75 (4): 921–5. doi:10.1021/ja01100a043.

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[isbn3-88763-075-0-1] Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.

[pmid14653967-2] Wang YH, Bai CX, Hong QY, Chen J (December 2003). "Anti-inflammatory effect of methoxyphenamine compound in rat model of chronic obstructive pulmonary disease". Acta Pharmacologica Sinica. 24 (12): 1324–7. PMID 14653967.

[3] Woodruff EH, Lambooy JP, Burt WE (April 1940). "Physiologically active amines. III. Secondary and tertiary β-phenylpropylamines and β-phenylisopropylamines". Journal of the American Chemical Society. 62 (4): 922–4. doi:10.1021/ja01861a060.

[4] Heinzelman RV (February 1953). "Physiologically active secondary amines. β-(o-Methoxyphenyl)-isopropyl-N-methylamine and related compounds". Journal of the American Chemical Society. 75 (4): 921–5. doi:10.1021/ja01100a043.

[1]

[2]

[3]

[4]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R03CB02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-(2-methoxyphenyl)-N-methylpropan-2-amine
CAS Number	93-30-1
PubChem CID	4117
ChemSpider	3974
UNII	J3Z5SRI26Z
CompTox Dashboard (EPA)	DTXSID0023292
ECHA InfoCard	100.002.035
Chemical and physical data
Formula	C₁₁H₁₇NO
Molar mass	179.263 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=CC=C1OC)NC
InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-6-4-5-7-11(10)13-3/h4-7,9,12H,8H2,1-3H3 Key:OEHAYUOVELTAPG-UHFFFAOYSA-N

Methoxyphenamine

Chemistry

See also

References