DL-Laudanosine Chemical Properties

Melting point:

115°C

Boiling point:

490.07°C (rough estimate)

Density 

1.1729 (rough estimate)

refractive index 

1.5614 (estimate)

storage temp. 

Store at -20°C

solubility 

DMSO : 100 mg/mL (279.77 mM)

form 

Solid

pka

7.80±0.40(Predicted)

color 

White to Light Beige

InChI

InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3

InChIKey

KGPAYJZAMGEDIQ-UHFFFAOYSA-N

SMILES

C1(CC2=CC=C(OC)C(OC)=C2)C2=C(C=C(OC)C(OC)=C2)CCN1C

LogP

3.630 (est)

Safety Information

Risk Statements 

26/28-40

Safety Statements 

22-24/25

RIDADR 

2810

HazardClass 

6.1(b)

PackingGroup 

III

DL-Laudanosine Usage And Synthesis

Description

This opium alkaloid occurs in the liquor following precipitation of Thebaine (q.v.) and is purified by extraction with small quantities of Et20, followed by precipitation with potassium iodide. The base crystallizes from hot C6H6 in small, colourless needles and has [α]¹⁵_D+ 103.23° (EtOH). It is freely soluble in CHCI3, EtOH, Et20 or hot C6H6 but insoluble in H20 or alkalies. No colour is produced with FeCl 3 but with Fe203 and H2S04, a brown colour is formed, changing to green when warmed to ISOoC. With concentrated H2S04 alone, the alkaloid gives a rose-red colour, changing to deep violet at ISO°C. The solution of the alkaloid in EtOH is alkaline to litmus and both it, and its salts, are bitter to the taste. The crystalline methiodide has m.p. 218-221°C; [α]_D + 120°. The oxidation products with Mn02 and H2S04 are veratraldehyde, 2:3:6:7- tetramethoxy-9: I O-dihydroanthracene and laudaline (4: S-dimethoxy-2: - methylaminoethylbenzaldehyde, m.p. 123-4°C. On exhaustive methylation it yields trimethylamine and laudanosene (tetramethoxy-o-vinylstilbene). Laudanosine is one of the most convulsant of the opium alkaloids but possesses only a slight analgesic action.

Chemical Properties

light yellow fine crystalline powder

Uses

DL-Laudanosine is an intermediate in synthesizing (S)-Laudanosine (L178525), a metabolite of the neuromuscular-blocking drugs Atracurium (A794500) and Cisatracurium (C496700) with potentially toxic systemic effects. It crosses the blood-brain barrier and may cause excitement and seizure activity.

Definition

ChEBI: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline is a member of isoquinolines.

Purification Methods

Crystallise these from EtOH. The (±)-picrate crystallises from EtOH with m 177-178o. The (-)-isomer has m 83-85o and

References

Pictet, Athanasescu., Ber., 33, 2347 (1900)
Pictet, Finkelstein., ibid, 42, 1979 (1909)
Pyman, Reynolds.,J. Chern. Soc., 97, 1324 (1910)
Kondo, Mori.,J. Ph arm. Soc., Japan, 51,615 (1931)
Craig, Tarbell., J. Amer. Chern. Soc., 70,2783 (1948)
Synthesis:
Pictet, Finkelstein., Compt. rend., 148,925 (1909)
Elliot.,J. Heterocycl. Chern., 7, 1229 (1970)
Pharmacology:
Zunz., Elements de Pharmacodynamie speciale, Tome I, 178, Masson & Co., Paris (1932)
Krueger, Eddy, Sumwalt., U.S. Public Health Reports, Suppl. 165, 1007 (1943)

DL-Laudanosine(1699-51-0)Related Product Information

• Atracurium Impurity 19
• PHENYL P-TOLYL SULFONE
• Atracurium Impurity 1
• Atracurium Impurity 41
• Atracurium Impurity 26 Besylate
• Cistracurium Besylate EP Impurity D
• Atracurium Impurity 18
• R-tetrahydropapaverine HCl
• 1,5-pentanediyl bis[1-[(3,4-dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate]
• AtracuriuM IMpurity V
• 6,7-Dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride
• (1R,2R)-1-[(3,4-Dimethoxyphenyl)methyl]-2-[3-(tert-butoxy)-3-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolinium benzenesulfonate
• Atracurium EP Impurity D
• Levonorgestrel Glycidol
• DL-LAUDANOSINE
• Cepharanthine
• DL-laudanosine hydrobromide trihydrate
• Atracurium besylate