ChemicalBook--->CAS DataBase List--->4579-64-0

4579-64-0

4579-64-0 Structure

4579-64-0 Structure
IdentificationBack Directory
[Name]

9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID METHYL ESTER
[CAS]

4579-64-0
[Synonyms]

Methyl Ergoline Acid
Lysergic acid methyl
Methyl Lysergic Acid
D-Lysergic Acid Methyl Ester
methyl 9,10-didehydro-6-methylergoline-8
methyl 9,10-didehydro-6-methylergoline-8beta-carboxylate
9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID METHYL ESTER
[EINECS(EC#)]

224-964-9
[Molecular Formula]

C17H18N2O2
[MDL Number]

MFCD07368163
[MOL File]

4579-64-0.mol
[Molecular Weight]

282.34
Chemical PropertiesBack Directory
[Melting point ]

164-166 °C(Solv: benzene (71-43-2))
[Boiling point ]

469.0±45.0 °C(Predicted)
[density ]

1.30±0.1 g/cm3(Predicted)
[storage temp. ]

-20°C Freezer
[solubility ]

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

17.25±0.40(Predicted)
[color ]

Pale Grey to Black
[InChI]

InChI=1/C17H18N2O2/c1-19-9-11(17(20)21-2)6-13-12-4-3-5-14-16(12)10(8-18-14)7-15(13)19/h3-6,8,11,15,18H,7,9H2,1-2H3/t11?,15-/s3
[InChIKey]

RNHDWLRHUJZABX-RXHCFGRJNA-N
[SMILES]

C12C3C=CC=C4NC=C(C[C@@]1([H])N(C)CC(C(OC)=O)C=2)C=34 |&1:10,r|
Hazard InformationBack Directory
[Description]

Lysergic acid methyl ester is an analogue of lysergic acid diethylamide (LSD). It is a member of the tryptamine family and is extremely uncommon. It acts on the 5-HT receptors in the brain, as do most tryptamines.
[Uses]

D-Lysergic Acid Methyl Ester is used in preparation of Serotonin agonists.It is an impurity of Lysergic Acid (L488000). Lysergic Acid and Iso-lysergic Acid are the main cleavage products formed on alkaline hydrolysis of the alkaloids which are characteristic of ergot. Potent hallucinogen; non-selective serotonin receptor agonist.
[Preparation]

synthesis of lysergic acid methyl ester: A suspension is prepared from 5.0 g of isolysergic acid amide in 80 ml of anhydrous methanol; the mixture is cooled to about -50°C and, under agitation, 40 ml of a 13N solution of hydrogen chloride in anhydrous methanol is added thereto. The clear solution is allowed to warm up to room temperature and further stirred overnight. The primary amount of the thus-formed ester hydrochloride is thus crystallized. By cooling in an ice bath and adding ethyl acetate, the crystallization is completed, and the precipitate is vacuum-filtered. Yield: 5.2 g (84% of theory) of lysergic acid methyl ester, hydrochloride.
Spectrum DetailBack Directory
[Spectrum Detail]

D-Lysergic Acid Methyl Ester(4579-64-0)1HNMR
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