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100-92-5

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100-92-5 Usage

Originator

Wyamine,Wyeth,US,1947

Uses

Different sources of media describe the Uses of 100-92-5 differently. You can refer to the following data:
1. Adrenergic (vasoconstrictor).
2. Mephentermine is an α-adrenergic agonist. Mephentermine is used as an antihypotensive.

Manufacturing Process

0.5 g of 2-(N-methylamino)-2-methyl-1-phenyl-1-propanol was treated with 1 cc of thionyl chloride at room temperature. A vigorous reaction set in. The gummy material was stirred with a small amount of petroleum ether and allowed to stand overnight. The brown crystalline solid after washing with petroleum ether was recrystallized from a small amount of absolute alcohol with addition of charcoal followed by filtration. On dilution with several volumes of ether and refrigeration white granular crystals of 1-chloro-2-(Nmethamino)-2-methyl-1-phenyl propane hydrochloride were deposited.250 mg of 1-chloro-2-(N-methylamino)-2-methyl-1-phenyl propane hydrochloride was dissolved in 2 cc of warm methanol and hydrogenated in the presence of 250 mg of palladium barium carbonate catalyst with provision for the absorption of the carbon-dioxide formed. When the theoretical amount of hydrogen had been taken up the mixture was filtered to remove the catalyst, concentrated to small volume and extracted with ether. After separating the ether the residue was further concentrated yielding a white crystalline solid. This solid on solution in water, strongly alkalizing, extraction with ether and removal of the ether yielded 2-(N-methylamino)-2-methyl-1- phenyl propane identified as the picrate by melting point 155°C to 156°C and mixed melting point 154.0°C to 154.5°C, with an authentic sample melting at 150°C to 153°C.

Brand name

Wyamine Sulfate (Baxter Healthcare).

Therapeutic Function

Adrenergic (vasopressor)

Check Digit Verification of cas no

The CAS Registry Mumber 100-92-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100-92:
(5*1)+(4*0)+(3*0)+(2*9)+(1*2)=25
25 % 10 = 5
So 100-92-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3

100-92-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name N,2-dimethyl-1-phenylpropan-2-amine

1.2 Other means of identification

Product number -
Other names Wyfentermina

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:100-92-5 SDS

100-92-5Synthetic route

β-Hydroxymephentermin
10079-55-7

β-Hydroxymephentermin

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
With thionyl chloride anschliessend Hydrierung des jeweils erhaltenen Reaktionsprodukts an Palladium/BaCO3 in Methanol;
With hydrogenchloride anschliessend Hydrierung des jeweils erhaltenen Reaktionsprodukts an Palladium/BaCO3 in Methanol;
N-(2-methyl-1-phenylpropan-2-yl)-1-phenylmethanimine
61765-66-0

N-(2-methyl-1-phenylpropan-2-yl)-1-phenylmethanimine

methyl iodide
74-88-4

methyl iodide

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
anschliessend mit wss. Aethanol;
oxethazaine
126-27-2

oxethazaine

A

mephentermine
100-92-5

mephentermine

B

<2-Hydroxy-aethyl>-
119483-39-5

<2-Hydroxy-aethyl>-

C

N-(1,1-Dimethyl-2-phenyl-ethyl)-N-methyl-2-(2-oxo-morpholin-4-yl)-acetamide

N-(1,1-Dimethyl-2-phenyl-ethyl)-N-methyl-2-(2-oxo-morpholin-4-yl)-acetamide

D

[{[(1,1-Dimethyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-(2-hydroxy-ethyl)-amino]-acetic acid

[{[(1,1-Dimethyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-(2-hydroxy-ethyl)-amino]-acetic acid

E

N-(1,1-Dimethyl-2-phenyl-ethyl)-2-[(2-hydroxy-ethyl)-methylcarbamoylmethyl-amino]-N-methyl-acetamide

N-(1,1-Dimethyl-2-phenyl-ethyl)-2-[(2-hydroxy-ethyl)-methylcarbamoylmethyl-amino]-N-methyl-acetamide

Conditions
ConditionsYield
at 90℃; for 2184h; Product distribution; other temperatures, other times, also in acidic solutions; stability under various conditions;
3'-Hydroxy-2-acetophenone hydrochloride

3'-Hydroxy-2-acetophenone hydrochloride

A

mephentermine
100-92-5

mephentermine

B

2-(1,1-Dimethyl-2-phenyl-ethylamino)-1-(3-hydroxy-phenyl)-ethanone

2-(1,1-Dimethyl-2-phenyl-ethylamino)-1-(3-hydroxy-phenyl)-ethanone

C

(Z)-1-(3-Hydroxy-phenyl)-ethene-1,2-diol

(Z)-1-(3-Hydroxy-phenyl)-ethene-1,2-diol

D

Phentermin
122-09-8

Phentermin

Conditions
ConditionsYield
at 37℃; metabolism;
2-Methyl-1-phenyl-2-propanol
100-86-7

2-Methyl-1-phenyl-2-propanol

sodium cyanide
143-33-9

sodium cyanide

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
(i) H2SO4, AcOH, (ii) /BRN= 1855608/, (iii) LiAlH4, Et2O; Multistep reaction;
(2-Chloro-1,1-dimethyl-2-phenyl-ethyl)-methyl-amine; hydrochloride

(2-Chloro-1,1-dimethyl-2-phenyl-ethyl)-methyl-amine; hydrochloride

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
With hydrogen; sodium acetate; nickel In methanol
benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

acetone-methylamine

acetone-methylamine

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
With diethyl ether
α-(1-amino-1-methylethyl)benzenemethanol
34405-42-0

α-(1-amino-1-methylethyl)benzenemethanol

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous hydriodic acid; phosphorus
3: anschliessend mit wss. Aethanol
View Scheme
Phentermin
122-09-8

Phentermin

mephentermine
100-92-5

mephentermine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: anschliessend mit wss. Aethanol
View Scheme
mephentermine
100-92-5

mephentermine

(2-cyclohexyl-1,1-dimethyl-ethyl)-methyl-amine
5368-87-6

(2-cyclohexyl-1,1-dimethyl-ethyl)-methyl-amine

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
mephentermine
100-92-5

mephentermine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

chloro-acetic acid-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]
2293-55-2

chloro-acetic acid-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

mephentermine
100-92-5

mephentermine

pentafluorobenzoylchloride
2251-50-5

pentafluorobenzoylchloride

N-(1,1-Dimethyl-2-phenyl-ethyl)-2,3,4,5,6-pentafluoro-N-methyl-benzamide

N-(1,1-Dimethyl-2-phenyl-ethyl)-2,3,4,5,6-pentafluoro-N-methyl-benzamide

mephentermine
100-92-5

mephentermine

N-Hydroxy-mephentermin
58670-93-2

N-Hydroxy-mephentermin

Conditions
ConditionsYield
(i) (PhCO)2O2, Et2O, (ii) LiAlH4; Multistep reaction;
mephentermine
100-92-5

mephentermine

5-chloro-3-phenyl-1,2,4-oxadiazole
827-44-1

5-chloro-3-phenyl-1,2,4-oxadiazole

(1,1-dimethyl-2-phenyl-ethyl)-methyl-(3-phenyl-[1,2,4]oxadiazol-5-ylmethyl)-amine

(1,1-dimethyl-2-phenyl-ethyl)-methyl-(3-phenyl-[1,2,4]oxadiazol-5-ylmethyl)-amine

mephentermine
100-92-5

mephentermine

heptafluorobutyric anhydride
336-59-4

heptafluorobutyric anhydride

N-(1,1-Dimethyl-2-phenyl-ethyl)-2,2,3,3,4,4,4-heptafluoro-N-methyl-butyramide

N-(1,1-Dimethyl-2-phenyl-ethyl)-2,2,3,3,4,4,4-heptafluoro-N-methyl-butyramide

mephentermine
100-92-5

mephentermine

ethyl (ethoxymethylene)cyanoacetate
94-05-3

ethyl (ethoxymethylene)cyanoacetate

Conditions
ConditionsYield
In ethanol Heating;
methanol
67-56-1

methanol

mephentermine
100-92-5

mephentermine

A

Formyl(N,α,α-trimethyl)phenylethylamin
78693-40-0

Formyl(N,α,α-trimethyl)phenylethylamin

B

Formyl(N-methoxymethyl-α,α-dimethyl)phenylethylamin

Formyl(N-methoxymethyl-α,α-dimethyl)phenylethylamin

Conditions
ConditionsYield
With potassium hydroxide at 20℃;
methanol
67-56-1

methanol

mephentermine
100-92-5

mephentermine

A

Formyl(N-methoxymethyl-α,α-dimethyl)phenylethylamin
78469-70-2

Formyl(N-methoxymethyl-α,α-dimethyl)phenylethylamin

B

Formyl(N,α,α-trimethyl)phenylethylamin

Formyl(N,α,α-trimethyl)phenylethylamin

Conditions
ConditionsYield
With potassium hydroxide at 20℃;
mephentermine
100-92-5

mephentermine

formaldehyde

formaldehyde

Conditions
ConditionsYield
With oxygen In water at 37℃; for 0.5h; rate of N-demethylation in the 9.000-g-supernatant of rat liver homogenates;
mephentermine
100-92-5

mephentermine

pyrrolidino-acetic acid-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

pyrrolidino-acetic acid-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: sodium carbonate; butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

N-(2-hydroxy-ethyl)-glycine-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]
2293-56-3

N-(2-hydroxy-ethyl)-glycine-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: Na2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

oxethazaine
126-27-2

oxethazaine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

<2-Hydroxy-aethyl>--
110272-39-4

<2-Hydroxy-aethyl>--

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

<2-Hydroxy-aethyl>--

<2-Hydroxy-aethyl>--

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

<2-Hydroxy-aethyl>--
122119-93-1

<2-Hydroxy-aethyl>--

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

(2-hydroxy-propylimino)-di-acetic acid bis-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]
97154-46-6

(2-hydroxy-propylimino)-di-acetic acid bis-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

(3-hydroxy-propylimino)-di-acetic acid bis-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]
116030-78-5

(3-hydroxy-propylimino)-di-acetic acid bis-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

(1-hydroxymethyl-propylimino)-di-acetic acid bis-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]
97084-93-0

(1-hydroxymethyl-propylimino)-di-acetic acid bis-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amide]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme
mephentermine
100-92-5

mephentermine

6-Hydroxy-hexylimino-bis-
103268-05-9

6-Hydroxy-hexylimino-bis-

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: K2CO3 / butan-1-ol
View Scheme

100-92-5Relevant articles and documents

-

Zenitz,Macks,Moore

, p. 955 (1948)

-

Stability of oxetacain and the structure of its degradation products

Gober,Franke,Lisowski

, p. 584 - 587 (2007/10/02)

Refluxed acid aqueous solutions of oxetacain (1) show 3 degradation products. 1 is decomposed at room temperature (20 °C, 480 d) 10%. 7 degradation products of crystalline 1 are detectable in the temperature-moisture test. At room temperature no other product than 1 appears. Under normal storage conditions a 5-year stability for acid aqueous solutions and a more than 10-year stability for crystalline 1 are estimated. Small amounts of the degradation products were isolated by TLC and HPLC. According to MS, UV and IR analysis their structures are mephentermin (2), a morpholinone derivative (3), a carboxylic acid derivative of 1 (4), a mono-C-demethyl-1 (5) and a mono-N-de(1-phenyl-2-methyl-propyl)-1 (6). The structures of 2 other degradation products are unknown. MS fragmentation mechanisms are discussed.

Synthesis of N-substituted phenethylamines and corresponding cyclohexyl analogs. Preliminary evaluation as bronchodilators.

Data,Skibbe,Kerley,Weaver

, p. 38 - 43 (2007/10/05)

-

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