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Scopolamine

Product Name
Scopolamine
CAS No.
51-34-3
Chemical Name
Scopolamine
Synonyms
Scopolamine powder;SEE;Scopoderm;Scop;PHLPP;C01851;PHLPP1;PLEKHE1;Atroquin;Atrochin
CBNumber
CB9875364
Molecular Formula
C17H21NO4
Formula Weight
303.35
MOL File
51-34-3.mol
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Scopolamine Property

Melting point:
59 ºC
alpha 
D20 -28° (c = 2.7)
Boiling point:
444.28°C (rough estimate)
Density 
1.31
refractive index 
1.5022 (estimate)
Flash point:
232.2℃
storage temp. 
-20°C
solubility 
Soluble in water, freely soluble in ethanol (96 per cent).
pka
7.55-7.81(at 25℃)
Water Solubility 
95g/L(15 ºC)
LogP
0.980
NIST Chemistry Reference
Scopolamine(51-34-3)
EPA Substance Registry System
Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (.alpha.S)- (51-34-3)
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Safety

Hazard Codes 
T+
Risk Statements 
26/27/28
Safety Statements 
25-45
RIDADR 
UN 1544PSN2 6.1 / PGII
HS Code 
29399990
Hazardous Substances Data
51-34-3(Hazardous Substances Data)
Toxicity
A belladonna plant alkaloid that exerts its pharmacodynamic effects by blocking muscarinic acetylcholine receptor sites. The s.c. LD50 of scopolamine hydrobromide in mice is 3.8 g/kg. Scopolamine crosses the blood brain barrier, and its antimuscarinic effects include, in therapeutic doses, drowsiness, euphoria, amnesia, fatigue, loss of REM sleep and, at higher doses, restlessness or even delirium. Scopolamine can be used to treat motion sickness and parkinsonian tremor. The effects of scopolamine may be greater in the CNS than atropine, and it may be a better antidote for organophosphate intoxication.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H318Causes serious eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0000483
Product name
Hyoscine
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0000483
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB1305348
Product name
ANTI-PHLPP1(N-TERMINAL) antibody produced in rabbit
Purity
purified immunoglobulin, buffered aqueous solution
Packaging
400μL
Price
$461
Updated
2023/01/07
TRC
Product number
S200005
Product name
Scopolamine
Packaging
500mg
Price
$380
Updated
2021/12/16
Biosynth Carbosynth
Product number
FS16424
Product name
Scopolamine
Packaging
1g
Price
$500
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0005085
Product name
SCOPOLAMINE
Purity
95.00%
Packaging
1G
Price
$1685.72
Updated
2021/12/16
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Scopolamine Chemical Properties,Usage,Production

Description

Scopolamine is a type of alkaloid that exists in a variety of Solanaceae plants such as Scopolia japonica, Datura metel L., and so on. It is the main active ingredient in these plants.
Apart from scopolamine, several other chemical ingredients also exist in Scopolia japonica, including hyoscyamine, anisodamine, anisodine, and so on. Hyoscyamine is an inhibitor of parasympathetic nerve, with the analgesic and antispasmodic functions, especially for sciatica, sometimes for the treatment of epilepsy, seasickness, etc., and its pharmacological effects are similar to atropine. However, its clinical application is less because of its toxicity. The clinical applications of anisodamine are treating infectious toxic shock, vascular disorders, various neuralgia, smooth muscle spasms, vertigo, fundus disorders and sudden deafness, and other diseases. It has definite curative effect and is widely used in clinical in China. Its synthetic product is called “654-2,” which now still is an effective drug to treat infectious shock and other vascular diseases. While anisodine is used to treat vascular headache, retinal vasospasm, ischemic optic neuritis, cerebrovascular disease, acute paralysis, central dysfunction caused by carbon monoxide poisoning, tremor, paralysis, bronchial asthma, motion sickness, organophosphorus pesticide poisoning, and so on .

Chemical Properties

White or almost white, crystalline powder or colourless crystals.

Physical properties

Appearance: a kind of viscous liquid, brown color. Solubility: soluble in ethanol, ethyl ether, chloroform, acetone, and water, very soluble in hot water, slightly soluble in benzene and petroleum ether, and also soluble in cold water. It can generate various crystals with multiple inorganic or organic acids. Melting point: 59±1.0?°C

History

Scopolamine is the main active ingredient of Scopolia japonica, Datura metel L., and other Solanaceae plants. As early as 1892, the chemist E.?Schmidt first isolated it from the Scopolia japonica, so named it as scopolamine. Due to its obvious deficiencies in solubility and usage, the researchers modified its structure as scopolamine butylbromide, which was synthesized and used scopolamine and bromo-n-butane with heating refluxing method. Preparation method of scopolamine butylbromide is simple, and it’s easy to be synthesized. There are about 170 domestic enterprises producing its raw materials currently.
European Pharmacopoeia (9th ed.), United States Pharmacopeia (36), and the Japanese Pharmacopoeia (16th ed.) contained bromine scopolamine; British Pharmacopoeia (2015) contained the raw materials and preparations of scopolamine butylbromide, including tablets and injections. Pharmacopoeia of the People’s Republic of China (2015) contained its raw materials, injection, and capsules.

Uses

Scopolamine is used for practically the same indications as atropine, but it should be noted that it has a sedative effect on motor activity, and it is recommended for the treatment of Parkinsonian symptoms.

Uses

cholinergic (ophthalmic).

Definition

ChEBI: A tropane alkaloid that is the (S)-tropic acid ester of 6beta,7beta-epoxy-1alphaH,5alphaH-tropan-3alpha-ol.

brand name

Isopto Hyoscine (Alcon); Transderm-Scop (Ciba-Geigy);Diban;Donnagel-pg;Donnatal;Phenacon;Ru-tuss;Scopoderm tts;Spasmofen;Susano;Tropax.

World Health Organization (WHO)

Scopolamine, an alkaloid with anticholinergic activity extracted from solanaceous plants, was introduced into medicine in 1888. It is used as a mydriatic, as an anti-emetic for the control of motion sickness, and for premedication in general anaesthesia. Shortly after their introduction in the early 1980's, transdermal delivery systems containing scopolamine that were indicated for the prevention of motion sickness were associated with visual disorders (e.g. mydriasis, glaucoma) and hallucinations. The action taken in Norway is in accordance with the legislation in several other countries where these preparations have always been subjected to prescription control.

General Description

Scopolamine (hyoscine) is found in variousmembers of the Solanaceae (e.g., H. niger, Duboisia myoporoides,Scopolia spp., and Datura metel). Scopolamineusually is isolated from the mother liquor remaining from theisolation of hyoscyamine.
Hyoscine is the older name for this alkaloid, althoughscopolamine is the accepted name in the United States.Scopolamine is the levo component of the racemic mixturethat is known as atroscine. The alkaloid is racemized readilyin the presence of dilute alkali.
The alkaloid occurs in the form of a levorotatory, viscousliquid that is only slightly soluble in water but very solublein alcohol, chloroform, or ether. It forms crystalline saltswith most acids, with the hydrobromide being the most stableand the most popularly accepted. An aqueous solution ofthe hydrobromide containing 10% mannitol is said to be lessprone to decomposition than unprotected solutions.

Pharmacology

Scopolamine butylbromide, a modified scopolamine, is a peripheral anti-choline drug; it not only can smooth muscle spasm but also block the ganglion and neuromuscular junction and has the weak effect on center. This drug has stronger effects on intestinal smooth muscle spasm than atropine and anisodamine; it can selectively relieve gastrointestinal tract, biliary tract, and urinary tract smooth muscle spasm and inhibit its peristalsis. Scopolamine butylbromide has less effects on the heart, pupil, and salivary gland, so it rarely induces central nervous excitement, dilation, inhibition of saliva secretion, and other adverse reactions, which is unlike atropine.
Scopolamine butylbromide is an antagonist of the M cholinergic receptor, its pharmacological effects are similar to atropine, but it has its own characteristics that have an obvious advantage in improving blood microcirculation.
Oral absorption of scopolamine butylbromide is not easy. It produces efficacy at 2–4?min after intravenous injection, 8–10?min after subcutaneous or intramuscular injection, and 20–30? min after oral administration, which could maintain about 2–6?h .

Clinical Use

The commercially available transdermal system of scopolaminecomprises an outer layer of polymer film and a drug reservoircontaining scopolamine, polyisobutylene, and mineral oil, which is interfaced with a microporous membrane tocontrol diffusion of the drug. In this dosage form, scopolamineis effective in preventing motion sickness. The actionis believed to be on the cortex or the vestibular apparatus.Whereas atropine stimulates the CNS, causing restlessnessand talkativeness, scopolamine usually acts as a CNSdepressant.

Safety Profile

Poison by intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by ingestion. Human systemic effects from very small amounts by subcutaneous and intramuscular routes: changes in surface EEG, dstorted perceptions, excitement, hallucinations, and mydriasis. It can cause the individual who is affected to lose a certain amount of his normal inhibitory control. It is for that reason that it has been called “truth serum.” An experimental teratogen. Experimental reproductive effects. Human mutation data reported. In many cases of poisoning from ths material, and even to a certain extent following its medcal application, there is retention of the urine caused by paralysis of the bladder, and catheterization is necessary. The fatal dose is variable. Death has occurred from as little as 0.6 mg, whde recovery has occurred from doses of 7-1 5 mg. An anticholinergc drug. When heated to decomposition it emits highly toxic fumes of NOx. See also ESTERS

Synthesis

Scopolamine, the L-9-methyl-3-oxa-9-azatricyclo[3.2.1.0.2,4]non-7-yl ester of |á-hydroxymethylphenylacetic acid (14.1.6), can be synthesized from tropenol (14.1.2) by oxidizing the double bond between carbon atoms C6 and C7 of the tropine ring, giving an epoxide derivative, scopine (14.1.5). Esterification of this product using tropic acid gives scopolamine (14.1.6) [7,8].

target

AChR | 5-HT3 receptor | M1 muscarinic receptor | M2 muscarinic receptor

Metabolism

It is almost completely metabolized in the liver and is excreted via the kidneys. Its elimination half-life is approximately 8 hours.

Purification Methods

Crystallise it from *benzene/pet ether, EtOH or H2O. It is polymorphic with m 165-166o and 190-191o. The racemate has m 56-57o (H2O), 37-38o (2H2O), syrup (anhydrous), l and d isomers can separate as syrups when anhydrous. [Beilstein 27 H 99, 102, 27 I 247-248, 27 II 43-44, 27 III/IV 1790.]

Scopolamine Preparation Products And Raw materials

Raw materials

Preparation Products

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Scopolamine Suppliers

Shanghai Zhiyun Biotechnology Co., Ltd
Tel
13119135307 13119135307
Email
cuichengbio@163.com
Country
China
ProdList
2589
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
55
BioBioPha Co., Ltd.
Tel
0871-65217109 13211707573;
Fax
0871-65215563
Email
y.liu@mail.biobiopha.com
Country
China
ProdList
5658
Advantage
65
T&W GROUP
Tel
021-61551611 13296011611
Fax
+86 21-50676805
Email
contact@trustwe.com
Country
China
ProdList
9900
Advantage
58
Artis Chemistry (Shanghai) Co. Ltd.
Tel
86-21-60936353
Fax
86-21-60936352
Country
China
ProdList
336
Advantage
58
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
0755-83725681-603
Fax
+86 755 28094224
Country
China
ProdList
4505
Advantage
50
Shanghai Tauto Biotech Co., Ltd.
Tel
021-51320588
Fax
0086-21-51320502
Email
tauto@tautobiotech.com
Country
China
ProdList
3989
Advantage
66
TargetMol Chemicals Inc.
Tel
021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7934
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81960175
Fax
+1-541-2553641
Email
min.he@cato-chem.com
Country
China
ProdList
1958
Advantage
55
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View Lastest Price from Scopolamine manufacturers

Sinoway Industrial co., ltd.
Product
Scopolamine 51-34-3
Price
US $0.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
0.99
Supply Ability
20 tons
Release date
2022-11-11
Hebei Yanxi Chemical Co., Ltd.
Product
Scopolamine 51-34-3
Price
US $50.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
100000
Release date
2023-09-11
Guangzhou Wanjiang Biotechnology Co., Ltd.
Product
Scopolamine 51-34-3
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.99%
Supply Ability
20tons
Release date
2023-06-04

51-34-3, ScopolamineRelated Search:


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