Scopolamine

ChemicalBook > CAS DataBase List > 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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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

Hebei Lingding Biotechnology Co., Ltd.

Product: Scopolamine 51-34-3
Price: US $86.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 9000kg/per week
Release date: 2022-01-14

51-34-3, ScopolamineRelated Search:

methylol cellulose CARBOXYMETHYLCELLULOSE SODIUM SALT Methylparaben Scopolamine hydrobromide Kresoxim-methyl Bensulfuron methyl METHYL THIOPHENE-2-CARBOXYLATE Scopolamine butylbromide 2-Hydroxyethyl methacrylate Tris(hydroxymethyl)aminomethane Trimethylolpropane Methyl acrylate Thiophanate-methyl 2-Hydroxyphenylacetic acid Scopolamine Hydrobromide Trihydrate SCOPOLAMINE N-OXIDE HYDROBROMIDE Methyl Phenylacetic acid

6,7-Epoxytropine tropate

Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)-9-methyl-3-oxa-9-azatricyclo3.3.1.02,4non-7-yl ester, (.alpha.S)-

1aH,5aH-Tropan-3a-ol, 6b,7b-epoxy-, (-)-tropate (ester) (8CI)

3-Oxa-9-azatricyclo[3.3.1.02,4]nonane, benzeneacetic acid deriv.

6b,7b-Epoxy-3a-tropanyl S-(-)-tropate

9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropate

Atrochin

Atroquin

Scopolamine, 98%, from Atropa belladonna L.

Hyoscyamine Sulfate Impurity 4（Hyoscyamine Sulfate EP Impurity D）

Hyoscine Butylbromide Impurity 1（Hyoscine Butylbromide EP Impurity A）（Hyoscine）

Atropine Impurity 6（Atropine EP Impurity F）

Hyoscine Butylbromide EP Impurity A（Hyoscine）

(S)-α-(Hydroxymethyl)benzeneacetic acid (1β,2α,4α,5β,7α)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl ester

6,7-Epoxytropine trpate

Scopolamine

C01851

Benzeneacetic acid, a-(hydroxymethyl)-, (1a,2b,4b,5a,7b)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (aS)- (9CI)

Benzeneacetic acid, a-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, [7(S)-(1a,2b,4b,5a,7b)]-

l-Scopolamine

Scop

Scopoderm TTS

SEE

Transcop

Tropic acid ester with scopine

(-)-Scopolamin

Scopolamine (base and/or unspecified salts)

9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-alpha-(hydroxymethyl)benzeneacetate

Benzeneacetic acid, a-(hydroxyMethyl)-, (1a,2b,4b,5a,7b)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, (aS)-

Scopolamine-d3 N-butyl bromide

Murocoll

Plexonal

Scopoderm

transderm-SCOP

ANTI-PHLPP1(N-TERMINAL) antibody produced in rabbit

KIAA0606

PHLPP

PHLPP1

PLEKHE1

9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl 3-hydroxy-2-phenylpropanoate

Scopolamine (Hyoscine)

Hyoscyamine EP Impurity D

Benzeneacetic acid, α-(hydroxymethyl)-, (1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (αS)-

HYOSCINE N BUTYL BROMIDE BP USP/EP/BP

Scopolamine USP/EP/BP

Scopolamine powder

(1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (S)-3-hydroxy-2-phenylpropanoate

Skopolamin

Atropine EP Impurity F（Hyoscyamine EP Impurity D）

Hyoscine Ph . Eur

51-34-3

Plant extract