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826-39-1

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826-39-1 Usage

Description

Mecamylamine hydrochloride, also known as Inversine, is a secondary amine and a non-competitive nicotinic acetylcholine receptor antagonist with preferential activity at the α3β4 subtype. It is a white, odorless, or practically odorless, crystalline powder that is highly stable and soluble in water. Mecamylamine hydrochloride was previously used to treat hypertension but is now more commonly used in basic nicotine research and as an aid to smoking cessation.

Uses

Used in Neuroscience Research:
Mecamylamine hydrochloride is used as a non-selective nicotinic acetylcholine receptor blocker in aortic body neurons and in MLO-Y4 cells. It is also used as an additive in extracellular saline during current-clamp recordings to reduce synaptic input.
Used in Smoking Cessation:
Mecamylamine hydrochloride is used as an aid to smoking cessation due to its ability to block neuronal nicotinic acetylcholine receptors, reducing the rewarding effects of nicotine and potentially decreasing cravings for cigarettes.
Used in Neuropsychiatric Disorders:
Mecamylamine hydrochloride has been reported to be effective in various nicotine-responsive neuropsychiatric disorders, although further research is needed to fully understand its potential applications in this area.
Used in Drug Delivery:
Mecamylamine hydrochloride is supplied as tablets for oral use, each containing 2.5 mg of the active ingredient. The tablets also contain inactive ingredients such as calcium phosphate, D&C Yellow 10, FD&C Yellow 6, lactose, magnesium stearate, cornstarch, and talc.
Used in Chemical Synthesis:
Mecamylamine hydrochloride's chemical properties, such as its stability and solubility in water, make it a potentially useful compound in the synthesis of other pharmaceuticals or chemical products.

Therapeutic Function

Antihypertensive

Biological Activity

Non-competitive nicotinic acetylcholine receptor antagonist. Displays antidepressant-like effects in mice.

Biochem/physiol Actions

Noncompetitive nicotinic acetylcholine receptor antagonist; preferentially blocks nicotinic receptors at autonomic ganglia; crosses blood-brain barrier.

Metabolism

Mecamylamine hydrochloride (Inversine) is a secondary amine and can therefore easily penetrate cell membranes. Its absorption from the gastrointestinal tract is more complete than that of the quaternary ammonium compounds. Mecamylamine is well absorbed orally and crosses both the blood-brain and placental barriers; its distribution is not confined to the extracellular space. High concentrations of the drug accumulate in the liver and kidney, and it is excreted unchanged by the kidney. In contrast to most of the highly ionized ganglionic blocking agents, mecamylamine can produce central nervous system effects, including tremors, mental confusion, seizures, mania, and depression.The mechanism by which these central effects are produced is unclear.Mecamylamine is rarely used today as an antihypertensive drug because it blocks both parasympathetic and sympathetic ganglia.

Check Digit Verification of cas no

The CAS Registry Mumber 826-39-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 6 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 826-39:
(5*8)+(4*2)+(3*6)+(2*3)+(1*9)=81
81 % 10 = 1
So 826-39-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H21N.ClH/c1-10(2)8-5-6-9(7-8)11(10,3)12-4;/h8-9,12H,5-7H2,1-4H3;1H

826-39-1 Well-known Company Product Price

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  • USP

  • (1376006)  Mecamylamine hydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 826-39-1

  • 1376006-200MG

  • 4,588.74CNY

  • Detail
  • Sigma

  • (M9020)  Mecamylamine hydrochloride  

  • 826-39-1

  • M9020-5MG

  • 537.03CNY

  • Detail
  • Sigma

  • (M9020)  Mecamylamine hydrochloride  

  • 826-39-1

  • M9020-25MG

  • 2,165.67CNY

  • Detail
  • Sigma

  • (M9020)  Mecamylamine hydrochloride  

  • 826-39-1

  • M9020-100MG

  • 6,546.15CNY

  • Detail

826-39-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Mecamylamine Hydrochloride

1.2 Other means of identification

Product number -
Other names Bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:826-39-1 SDS

826-39-1Synthetic route

(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

(S)-phenylethyl isocyanate
14649-03-7

(S)-phenylethyl isocyanate

A

(1S,2R,4R)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine

(1S,2R,4R)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine

B

(1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine
107485-87-0

(1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine

Conditions
ConditionsYield
With sodium carbonate 2.) CHCl3, 1 h, room t.; Yield given. Multistep reaction. Yields of byproduct given;
ethyl bromide
74-96-4

ethyl bromide

(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

N-ethyl mecamylamine

N-ethyl mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

benzyl chloride
100-44-7

benzyl chloride

N-benzyl mecamylamine

N-benzyl mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

N-cyclopropylmethyl mecamylamine

N-cyclopropylmethyl mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

allyl bromide
106-95-6

allyl bromide

N-allyl mecamylamine

N-allyl mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

propargyl bromide
106-96-7

propargyl bromide

N-propargyl mecamylamine

N-propargyl mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

1-chloromethyl-4-fluorobenzene
352-11-4

1-chloromethyl-4-fluorobenzene

N-(4-fluorobenzyl) mecamylamine

N-(4-fluorobenzyl) mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

N-(4-nitrobenzyl) mecamylamine

N-(4-nitrobenzyl) mecamylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;
(+/-)-exo-mecamylamine hydrochloride
826-39-1

(+/-)-exo-mecamylamine hydrochloride

S-(+)-mecamylamine hydrochloride

S-(+)-mecamylamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) aq. Na2CO3 / 2.) CHCl3, 1 h, room t.
2: 64 percent / ethanol / 0.75 h / Heating
View Scheme

826-39-1Upstream product

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