9216. Tetrahydropapaveroline

Nomenclature

CAS number: 4747-99-3
1-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-isoquinolinediol; 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.
C16H17NO4; mol wt 287.31.
C 66.89%, H 5.96%, N 4.88%, O 22.27%.

Description and 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).

Chemical structure

Derivative

(±)-Form hydrochloride.
C16H18ClNO4; mol wt 323.77.
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.

Derivative

(-)-Form hydrochloride.

Properties

Cryst from 6N HCl, mp 285-286°. [α]D25 -32.4° (c = 1 in water). uv max (ethanol): 230, 286 nm (ε 11100, 6700).

Derivative

(+)-Form hydrochloride.

Properties

Cryst, mp 285-286°. [α]D25 +32.1° (c = 1 in water).

Use

As a research tool in neurological biochemistry.