DL-Laudanosine

ChemicalBook > CAS DataBase List > DL-Laudanosine

Product Name: DL-Laudanosine
CAS No.: 1699-51-0
Chemical Name: DL-Laudanosine
Synonyms: DL-LAUDANOSINE;DL-LAUDANOSIDE;(R)-Laudanosine;Laudanosine CRS;(+-)-laudanosine;LAUDANOSINE, DL-;(+/-)-LAUDANOSIDE;DL-Laudanosine,99%;LAUDANOSINE, DL-(SH);Atracurium Impurity 42
CBNumber: CB9423783
Molecular Formula: C21H27NO4
Formula Weight: 357.44
MOL File: 1699-51-0.mol

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DL-Laudanosine Property

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)

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Safety

Risk Statements: 26/28-40
Safety Statements: 22-24/25
RIDADR: 2810
HazardClass: 6.1(b)
PackingGroup: III

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P311Call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P363Wash contaminated clothing before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: L178540
Product name: DL-Laudanosine
Packaging: 100mg
Price: $490
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FL52345
Product name: DL-Laudanosine
Packaging: 50mg
Price: $80
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FL52345
Product name: DL-Laudanosine
Packaging: 100mg
Price: $130
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FL52345
Product name: DL-Laudanosine
Packaging: 250mg
Price: $200
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FL52345
Product name: DL-Laudanosine
Packaging: 500mg
Price: $350
Updated: 2021/12/16

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DL-Laudanosine Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from DL-Laudanosine manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Atracurium Impurity 42
Price: US $0.00-0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 10g
Release date: 2024-04-10

1699-51-0, DL-LaudanosineRelated Search:

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

(+-)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline

(+-)-laudanosine

2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-(+-)-isoquinolin

N-METHYLTETRAHYDROPAPAVERINE

DL-LAUDANOSIDE

DL-LAUDANOSINE

(+/-)-LAUDANOSIDE

LAUDANOSINE, DL-

(±)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

DL-LAUDANOSINE, FREE BASE

(1R)-1,2,3,4-Tetrahydro-2-methyl-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline

(R)-Laudanosine

DL-Laudanosine,99%

LAUDANOSINE, DL-(SH)(CALL)

DL-LAUDANOSINE(WXG01661)

LAUDANOSINE, DL-(SH)

1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Laudanosine CRS

Atracurium Impurity 42

Atracurium besilate EP Impurity G

Cisatracurium Besylate Impurity 47

Laudanosine (Y0001765)

Cisatracurium Besilate Impurity 10

Atracurium EP Impurity G (DL-Laudanosine)

Drug Metabolite,DLLaudanosine,DL Laudanosine,DL-Laudanosine,Inhibitor,inhibit

Atracurium Impurity 42 (Atracurium Besilate EP Impurity G)

1699-51-0

C21H27NO4