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methyl(2,3,3-trimethyltrinorbornan-2-yl)amine structure

methyl(2,3,3-trimethyltrinorbornan-2-yl)amine
  • CAS：60-40-2
  • MW:167.296
  • MF：C11H21N
Antihypertensive.
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1. Names and Identifiers
1.1 Name
methyl(2,3,3-trimethyltrinorbornan-2-yl)amine
1.2 Synonyms
2-Methylamino-2,3,3-trimethylnorbornane; EINECS 200-476-1; Mecamine; MECAMYLAMINE BASE; Mekamine; Mevasine; N,2,3,3-Tetramethyl-2-norbornanamine; Plegangin;
1.3 CAS No.
60-40-2
1.4 CID
4032
1.5 EINECS
200-476-1
1.6 Molecular Formula
C11H21N
1.7 Inchi
InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
1.8 InChkey
IMYZQPCYWPFTAG-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1(C2CCC(C2)C1(C)NC)C
1.10 Isomers Smiles
CC1(C2CCC(C2)C1(C)NC)C
2. Properties
2.1 Solubility
1.24e-01 g/L
2.2 Physical
Solid
2.3 Water Solubility
1.24e-01 g/L
3. Use and Manufacturing
3.1 Description
Solid
3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501
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3.3 Usage
Antihypertensive.
4. Safety and Handling
4.1 Safety

Poison by ingestion, subcutaneous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.

4.2 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 40mg/kg (40mg/kg) BEHAVIORAL: SLEEP Archivum Immunologiae et Therapiae Experimentalis. Vol. 10, Pg. 905, 1962.
mouse LD50 intravenous 11900ug/kg (11.9mg/kg)   United States Patent Document. Vol. #4168308,
mouse LD50 oral 90mg/kg (90mg/kg)   Bollettino Chimico Farmaceutico. Vol. 103, Pg. 490, 1964.
mouse LD50 subcutaneous 37500ug/kg (37.5mg/kg)   Farmakologiya i Toksikologiya Vol. 25, Pg. 163, 1962.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 4

Specific target organ toxicity – single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H312 Harmful in contact with skin

H315 Causes skin irritation

H319 Causes serious eye irritation

H332 Harmful if inhaled

H335 May cause respiratory irritation
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/…if you feel unwell.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P332+P313 If skin irritation occurs: Get medical advice/attention.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Computed Properties
7.Other Information
Originator
Inversine ,MSD ,US ,1956
Uses
Antihypertensive.
Manufacturing Process
Preparation of 2-(N-Formylamino)Isocamphane: Into a 5-liter 3-necked round bottom flask equipped with stirrer, dropping funnel and thermometer, was added 325 ml of glacial acetic acid. Then, portionwise, a total of 133 g of sodium cyanide (granular, 2.6 mols) was added with stirring while holding the temperature at 15°C. To the thick white slurry was added dropwise a previously prepared cold mixture of 325 ml glacial acetic acid and 360 ml concentrated sulfuric acid.
After addition of a few milliliters at 15°C, the thick slurry thins slowly and the remainder of the sulfuric-glacial acetic acid mixture was added at 0° to 2°C. A total of about 2 hours was required for the addition. After addition, stirring was continued for 15 minutes, Then dropwise, over an hour, a solution of 178 g (1.3 mold of dl-camphene in 50 ml of glacial acetic acid was added while keeping the temperature at about 0°C (±3°C).
Stirring was continued for two hours at 0°C during which time a slight pinkish-yellow color developed in the reaction mixture. The cooling bath was removed and the temperature allowed to rise to 15° to 20°C in about 2 to 3 hours. The ice bath was then re placed and while holding the temperature at about 20°C, the mixture was gradually diluted with 3 liters of water while stirring vigorously. After an hour or two of good agitation at room temperature, the oily product was extracted with 2 x 500 ml and 1 x 200 ml of chloroform and the combined extracts washed with 2 x 500 ml of water. The chloroform extract was then rendered neutral by stirring with 500 ml water and gradually adding solid sodium bicarbonate to the mixture until the aqueous phase had a pH of about 7; required, approximately 88 g of NaHCO3.
After separation the chloroform layer was washed with 2 x 500 ml water, dried over calcium chloride, and after filtration the solvent was removed in vacuo on the steam bath. A solid somewhat sticky residue of 231.2 g was obtained. After removal of last traces of chloroform by repeated swishing with petroleum ether, the cake was finally refluxed with about 500 ml petroleum ether (BP 30° to 60°C) until a thick crystalline slurry was obtained. After refrigeration for a day, the white crystalline mass was filtered by suction, washed with petroleum ether (2 x 125 ml), then n-heptane (2 x 125 ml) and again with petroleum ether (2 x 125 ml). After air drying at room temperature to constant weight, 180.6 g of the dl-2-(N-formylamino)isocamphane melting at 160° to 165°C was obtained.
The combined petroleum ether and n-heptane washes were concentrated under diminished pressure and the residual oil dissolved in a minimum amount of hot petroleum ether (about 75 ml). The resulting solution was placed in the refrigerator for two days. The precipitated dl-2-(N-formylamino) isocamphane was then recovered by filtration and washed with petroleum ether and n-heptane as described above. Obtained, 12.6 g of product having a MP of 158° to 164°C.
The dl-2-(N-formylamino)isocamphane (193 g) was dissolved in 1.9 liters nheptane by heating on a steam bath, After clarifying the solution by filtration, the clear filtrate was allowed to stand at room temperature until crystallization was complete. The crystalline product is filtered by suction, washed with a little cold n-heptane and air dried. The dl-2-(N-formylamino)isocamphane melted at 169° to 174°C.
Preparation of 2-(N-Methylamino)Isocamphane: To 4.23 liters of anhydrous ether in a 12-liter 3-necked flask fitted with a stirrer, reflux condenser and dropping funnel was quickly added 78 g (2.05 mols) of lithium aluminum hydride. The mixture was gently refluxed with stirring until all hydride had dissolved which required several hours.
A solution of 168 g (0.92 mol) of dl-2-(N-formylamino)isocamphane, prepared as described above, in 1.81 liters of anhydrous ether was then added during a period of about one hour with stirring. After addition, the mixture was refluxed for about 6 hours after which it was cooled slightly and 347 ml of water added with stirring, hydrogen gas being evolved during the addition, Stirring was continued until the precipitate changed to a powder, which was filtered by suction and washed with ether (a total of about 2 liters).
The combined filtrate and washes were concentrated to 1.6 liters and the concentrate containing the dl-2-(N-methylamino)isocamphane washed once with about 350 cc water, and then dried over anhydrous sodium sulfate. The dried ether concentrate was then cooled in an ice bath and with stirring a cold saturated ethereal-hydrogen chloride solution was added slowly until acid to Congo red; required, about 440 ml anhydrous ether saturated (at 0°C) with HCl gas, After precipitation was complete, the white crystalline dl-2-(Nmethylamino)isocamphane hydrochloride was filtered, and washed with anhydrous ether (about 1 liter) until the washes were neutral. The dl-2-(Nmethylamino)isocamphane hydrochloride was air dried at room temperature. Obtained, 156.5 g of product melting with decomposition at 249°C.
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8. Toltal 12 Suppliers View more
Mecamylamine
Pure Chemistry Scientific Inc.
United States
Tel: Update Time:2019/02/25
inquire
TIANFU-CHEM 60-40-2 methyl(2,3,3-trimethyltrinorbornan-2-yl)amine
Antimex Chemical Limied
China
Tel: Update Time:2019/02/24
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Mecamylamine
MENGNA
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Mecamylamine
Tianjin Harmony Technology Development Co., Ltd.
China
Tel: Update Time:2010/08/12
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MecaMylaMine
Beijing HuaMeiHuLiBiological Chemical
China
Tel: Update Time:2019/11/26
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9. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. Computational chemical data
7. Other Information
8. Toltal 12 Suppliers
9. Realated Product Infomation
 
 
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