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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]15D+ 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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DL-Laudanosine Suppliers

China 53 Czech 1 France 1 Germany 2 India 3 South Korea 1 Switzerland 3 Ukraine 1 United Kingdom 6 United States 15 Global 86
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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