Macromerine
Title: Macromerine
CAS Registry Number: 2970-95-8
CAS Name: a-[(Dimethylamino)methyl]-3,4-dimethoxybenzenemethanol
Additional Names: a-[(dimethylamino)methyl]veratryl alcohol; 3,4-dimethoxy-a-[(dimethylamino)methyl]benzyl alcohol; dimethylaminomethyl 3,4-dimethoxyphenyl carbinol
Molecular Formula: C12H19NO3
Molecular Weight: 225.28
Percent Composition: C 63.98%, H 8.50%, N 6.22%, O 21.31%
Literature References: Prepn of dl-form: La Manna et al., Farmaco Ed. Sci. 15, 9 (1960); Chapman et al., Proc. R. Soc. London Ser. B 163, (990), 116 (1965); Hodgkins et al., Tetrahedron Lett. 1967, 1321; of d- and l-forms: La Manna et al., loc. cit. Isoln of l-form from cactus, Coryphantha macromeris (Engelm.) Lem., Britton and Rose, Cactaceae: Hodgkins et al., loc. cit.
 
Derivative Type: dl-Form
Properties: Crystals, mp 46-47°.
Melting point: mp 46-47°
 
Derivative Type: l-Form
Properties: Crystals, mp 66-67.5°. [a]D25 -147.01° (c = 0.0390 g/ml chloroform), -42.61° (c = 0.0200 g/ml abs alcohol).
Melting point: mp 66-67.5°
Optical Rotation: [a]D25 -147.01° (c = 0.0390 g/ml chloroform), -42.61° (c = 0.0200 g/ml abs alcohol)
 
Derivative Type: d-Form
Properties: Crystals, mp 60-62°.
Melting point: mp 60-62°
 
Derivative Type: dl-Form hydrochloride
Molecular Formula: C12H19NO3.HCl
Molecular Weight: 261.75
Percent Composition: C 55.06%, H 7.70%, N 5.35%, O 18.34%, Cl 13.54%
Properties: Crystals from ethanol, mp 163-164°.
Melting point: mp 163-164°
 
Derivative Type: l-Form hydrochloride
Properties: Crystals, mp 178-179°. [a]D18 -41.3° (c = 2.04 in 50% ethanol).
Melting point: mp 178-179°
Optical Rotation: [a]D18 -41.3° (c = 2.04 in 50% ethanol)
 
Derivative Type: d-Form hydrochloride
Properties: Crystals from ethanol, mp 178- 179°. [a]D18 +51.5° (c = 2.2 in 50% ethanol).
Melting point: mp 178- 179°
Optical Rotation: [a]D18 +51.5° (c = 2.2 in 50% ethanol)
 
NOTE: Both the dl- and l-forms are physiologically active, and caused hallucinogenic reactions when tested in animals (Hodgkins et al., loc. cit.).

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