Tetrahydropapaveroline
Title: Tetrahydropapaveroline
CAS Registry Number: 4747-99-3
CAS Name: 1-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-isoquinolinediol
Additional Names: 1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol; 6,7-dihydroxy-1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline; norlaudanosoline; THP
Molecular Formula: C16H17NO4
Molecular Weight: 287.31
Percent Composition: C 66.89%, H 5.96%, N 4.88%, O 22.27%
Literature References: Alkaloid deriv of dopamine and a biosynthetic precursor of morphine, q.v. Prepn of the racemic hydrochloride: F. L. Pyman, J. Chem. Soc. 95, 1610 (1909); of the (+)- and (-)-form hydrochlorides: S. Teitel et al., J. Med. Chem. 15, 845 (1972). Chromatographic study: K. D. McMurtrey et al., J. Liq. Chromatogr. 3, 663 (1980). Possible role of THP in the biochemical mediation of alcohol addiction: V. E. Davis, M. J. Walsh, Science 167, 1005 (1970); G. Cohen, M. Collins, ibid. 1749; R. D. Meyers, C. L. Melchior, ibid. 196, 554 (1977); M. Sandler et al., Prog. Clin. Biol. Res. 90, 215 (1982). Biosynthetic study: D. K. Choudhary, B. L. Kaul, Indian Drugs 19, 229 (1982). In vivo and in vitro effects on rat pituitary function: D. R. Britton et al., Biochem. Pharmacol. 31, 1205 (1982). Effect on dopaminergic neurons: I. S. Hoffman, L. X. Cubeddu, J. Pharmacol. Exp. Ther. 220, 16 (1982). Comparison to opioid effects in brain regions: G. R. Siggins et al., Prog. Clin. Biol. Res. 90, 275 (1982).
 
Derivative Type: (±)-Form hydrochloride
Molecular Formula: C16H18ClNO4
Molecular Weight: 323.77
Percent Composition: C 59.35%, H 5.60%, Cl 10.95%, N 4.33%, O 19.77%
Properties: Colorless microscopic prisms, mp 291-293° (dec). Practically insol in water, alc.
Melting point: mp 291-293° (dec)
 
Derivative Type: (-)-Form hydrochloride
Properties: Cryst from 6N HCl, mp 285-286°. [a]D25 -32.4° (c = 1 in water). uv max (ethanol): 230, 286 nm (e 11100, 6700).
Melting point: mp 285-286°
Optical Rotation: [a]D25 -32.4° (c = 1 in water)
Absorption maximum: uv max (ethanol): 230, 286 nm (e 11100, 6700)
 
Derivative Type: (+)-Form hydrochloride
Properties: Cryst, mp 285-286°. [a]D25 +32.1° (c = 1 in water).
Melting point: mp 285-286°
Optical Rotation: [a]D25 +32.1° (c = 1 in water)
 
Use: As a research tool in neurological biochemistry.

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