Ajmaline supplier | CasNO.4360-12-7

Name
Ajmaline
EINECS 224-439-4
CAS No. 4360-12-7
Density 1.373 g/cm³
Solubility 489.7mg/L(30 oC)
Melting Point 189 °C
Formula C₂₀H₂₆N₂O₂
Boiling Point 519.406 °C at 760 mmHg
Molecular Weight 326.48
Flash Point 285.155 °C
Transport Information UN 1544
Appearance White solid
Safety 13-45-36
Risk Codes 25-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms Rhytmaton;Ajmalan-17,21-.alpha.diol;Ajmalan-17,21-diol, (17R,21alpha)-, compound with methanol (1:1);(17R,21-alpha)-Ajmalan-17,21-diol;Rauwolfine;Merabitol;Rauwolfin;Cardiorythmine;Rytmalin;Cartagine;Aritmina;Gilurytmal;Tachmalin;
PSA 46.94000
LogP 1.55740

Synthetic route

: 19775-56-5
diacetyl ajmaline

: 4360-12-7
(+)-ajmaline

Conditions

Conditions	Yield
With potassium carbonate In methanol for 48h; Ambient temperature;	93%

: 143065-03-6
(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole

: 4360-12-7
(+)-ajmaline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: H2 / 10 percent Pd/C / 1,2-dimethoxy-ethane / 48 h / 760 Torr 2: DMAP / 1,2-dimethoxy-ethane / 2 h 3: aq. conc. HCl / acetic acid / 3 h / Ambient temperature 4: HCl(g) / 48 h / Ambient temperature 5: 35.6 percent / BF3*Et2O, H2 / PtO2 / CH2Cl2 / 24 h / 760 Torr 6: 93 percent / aq. K2CO3 / methanol / 48 h / Ambient temperature View Scheme

: 210533-30-5
21-O-acetylajmalal A ethylene acetal

: 4360-12-7
(+)-ajmaline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. conc. HCl / acetic acid / 3 h / Ambient temperature 2: HCl(g) / 48 h / Ambient temperature 3: 35.6 percent / BF3*Et2O, H2 / PtO2 / CH2Cl2 / 24 h / 760 Torr 4: 93 percent / aq. K2CO3 / methanol / 48 h / Ambient temperature View Scheme

: (2S,3S,4R,6S,12aR,12bS,13S)-3-Ethyl-4,12a-dihydroxy-12-methyl-1,3,4,7,7a,12,12a,12b-octahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carbaldehyde

: 4360-12-7
(+)-ajmaline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl(g) / 48 h / Ambient temperature 2: 35.6 percent / BF3*Et2O, H2 / PtO2 / CH2Cl2 / 24 h / 760 Torr 3: 93 percent / aq. K2CO3 / methanol / 48 h / Ambient temperature View Scheme

: C22H28N2O3

: 4360-12-7
(+)-ajmaline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: DMAP / 1,2-dimethoxy-ethane / 2 h 2: aq. conc. HCl / acetic acid / 3 h / Ambient temperature 3: HCl(g) / 48 h / Ambient temperature 4: 35.6 percent / BF3*Et2O, H2 / PtO2 / CH2Cl2 / 24 h / 760 Torr 5: 93 percent / aq. K2CO3 / methanol / 48 h / Ambient temperature View Scheme

: 210533-31-6
2-epihydroxydiacetylajmaline

: 4360-12-7
(+)-ajmaline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 35.6 percent / BF3*Et2O, H2 / PtO2 / CH2Cl2 / 24 h / 760 Torr 2: 93 percent / aq. K2CO3 / methanol / 48 h / Ambient temperature View Scheme

: 4360-12-7
(+)-ajmaline

: (+)-21-Desoxy-dihydroajmalin

Conditions

Conditions	Yield
With hydrazine	96%

: 4360-12-7
(+)-ajmaline

: C20H25N3O

Conditions

Conditions	Yield
With air; hydroxylamine hydrochloride In ethanol Ring cleavage; oxidation; Heating;	89%

: 4360-12-7
(+)-ajmaline

: 106-94-5
propyl bromide

: N(4)-propylajmalinium bromide

Conditions

Conditions	Yield
In ethanol at 70 - 75℃; for 6h;	81.9%

: 71001-09-7
1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose

: 4360-12-7
(+)-ajmaline

: C32H44N2O7

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 12h; Ambient temperature;	80%

: 4360-12-7
(+)-ajmaline

: 38993-99-6
(6S,13S)-4-ethyl-6,7,12,13-tetrahydro-7-methyl-6,13-imino-5H-pyrido[3',4':5,6]cyclooct[1,2-b]indole

Conditions

Conditions	Yield
With air; hydroxylamine hydrochloride In butan-1-ol Oxidation; ring cleavage; cyclization; Heating;	30%

: 4360-12-7
(+)-ajmaline

: 141810-20-0
19(S)-hydroxy-Nβ-methylraumacline

Conditions

Conditions	Yield
Rauwolfia serpentina Benth. cell suspension culture;
Multi-step reaction with 13 steps 1: molecular sieves, H2SO4 / ethanol / 3 h / Heating 2: 1 N NaOH / CH2Cl2 / 0.5 h / Ambient temperature 3: 84 percent / CuCl2 / tetrahydrofuran; H2O / Ambient temperature; phosphate buffer pH 7 4: 71 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C 5: 78 percent / N-bromosuccinimide / tetrahydrofuran / 2 h / -22 °C 6: 71 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / dimethylformamide / 65 h / Ambient temperature 7: 98 percent / NaBH4 / methanol / 0.67 h / Ambient temperature 8: 100 percent / Et3N, p-dimethylaminopyridine / CH2Cl2 / 22 h / Ambient temperature 9: 1) BH3-Me2S, 2) 3 N aq. NaOH, 31percent H2O2 / 1) THF, r.t., 2.5 h, 2) 80 to 90 deg C, 1 h 10: 96 percent / n-Bu4NF / tetrahydrofuran / 40 h / Ambient temperature 11: 88 percent / Pb(OAc)4 / CH2Cl2 / 2.5 h / -70 °C 12: H2 / 10percent Pd/C / methanol / 4.5 h / 760 Torr 13: NaBHrCN, AcOH / H2O / 3 h View Scheme

Yield

Rauwolfia serpentina Benth. cell suspension culture;

Multi-step reaction with 13 steps
1: molecular sieves, H2SO4 / ethanol / 3 h / Heating
2: 1 N NaOH / CH2Cl2 / 0.5 h / Ambient temperature
3: 84 percent / CuCl2 / tetrahydrofuran; H2O / Ambient temperature; phosphate buffer pH 7
4: 71 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C
5: 78 percent / N-bromosuccinimide / tetrahydrofuran / 2 h / -22 °C
6: 71 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / dimethylformamide / 65 h / Ambient temperature
7: 98 percent / NaBH4 / methanol / 0.67 h / Ambient temperature
8: 100 percent / Et3N, p-dimethylaminopyridine / CH2Cl2 / 22 h / Ambient temperature
9: 1) BH3-Me2S, 2) 3 N aq. NaOH, 31percent H2O2 / 1) THF, r.t., 2.5 h, 2) 80 to 90 deg C, 1 h
10: 96 percent / n-Bu4NF / tetrahydrofuran / 40 h / Ambient temperature
11: 88 percent / Pb(OAc)4 / CH2Cl2 / 2.5 h / -70 °C
12: H2 / 10percent Pd/C / methanol / 4.5 h / 760 Torr
13: NaBHrCN, AcOH / H2O / 3 h
View Scheme

: 4360-12-7
(+)-ajmaline

: 115438-55-6
ajmaline-21-carboxylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide slightly acidic condition, on boiling water bath;

: 4360-12-7
(+)-ajmaline

: 6989-79-3
(+)-Isoajmalin

Conditions

Conditions	Yield
With potassium hydroxide In methanol	900 mg

: 4360-12-7
(+)-ajmaline

: 68622-80-0
ajmaline-Nb-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide Yield given;

: 4360-12-7
(+)-ajmaline

: 501-53-1
benzyl chloroformate

: C28H32N2O4

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 4360-12-7
(+)-ajmaline

: 57-14-7
1,1-dimethylhydrazine

: 2552-93-4
C22H32N4O

Conditions

Conditions	Yield
With 3 A molecular sieve; sulfuric acid In ethanol for 5h; Heating;
With molecular sieve; sulfuric acid In ethanol for 3h; Heating;

: 4360-12-7
(+)-ajmaline

: 74-88-4
methyl iodide

: Nb-methylajmaline

Conditions

Conditions	Yield
In acetonitrile for 1h; Heating;	9.8 mg

: 2417-90-5
bromopropionitrile

: 4360-12-7
(+)-ajmaline

: C23H30N3O2(1+)*Br(1-)

: 34723-82-5, 130233-15-7, 130233-16-8
2-(bromomethyl)tetrahydro-2H-pyran

: 4360-12-7
(+)-ajmaline

: C26H37N2O3(1+)*Br(1-)

: 693-58-3
1-Bromononane

: 4360-12-7
(+)-ajmaline

: N(b)-nonylajmaline bromide

Conditions

Conditions	Yield
In chloroform; acetonitrile for 8h; Heating;	1.2 g

: 629-27-6
1-Iodooctane

: 4360-12-7
(+)-ajmaline

: C28H43N2O2(1+)*I(1-)

: 111-25-1
1-bromo-hexane

: 4360-12-7
(+)-ajmaline

: C26H39N2O2(1+)*Br(1-)

: 43161-11-1
5-iodo-2-methylpent-2-ene

: 4360-12-7
(+)-ajmaline

: C26H37N2O2(1+)*I(1-)

: 4360-12-7
(+)-ajmaline

: 109-64-8
1,3-dibromo-propane

: C23H32BrN2O2(1+)*Br(1-)

: 70117-25-8
methyl 5-(bromomethyl)-furan-2-carboxylate

: 4360-12-7
(+)-ajmaline

: C27H33N2O5(1+)*Br(1-)

: 110-52-1
1,4-dibromo-butane

: 4360-12-7
(+)-ajmaline

: C24H34BrN2O2(1+)*Br(1-)

: 112-29-8
1-bromo dodecane

: 4360-12-7
(+)-ajmaline

: C30H47N2O2(1+)*Br(1-)

Conditions

Conditions	Yield
Heating;

: 74-96-4
ethyl bromide

: 4360-12-7
(+)-ajmaline

: C22H31N2O2(1+)*Br(1-)

: 542-69-8
1-iodo-butane

: 4360-12-7
(+)-ajmaline

: C24H35N2O2(1+)*I(1-)

: 4360-12-7
(+)-ajmaline

: 106-93-4
ethylene dibromide

: C22H30BrN2O2(1+)*Br(1-)

: 4360-12-7
(+)-ajmaline

: 3132-64-7
1,2-Epoxy-3-bromopropane

: C23H31N2O3(1+)*Br(1-)

: 693-67-4
bromoundecane

: 4360-12-7
(+)-ajmaline

: C31H49N2O2(1+)*Br(1-)

Conditions

Conditions	Yield
Heating;

: 112-71-0
1-Bromotetradecane

: 4360-12-7
(+)-ajmaline

: C34H55N2O2(1+)*Br(1-)

Conditions

Conditions	Yield
Heating;

: 4282-40-0
1-Iodoheptane

: 4360-12-7
(+)-ajmaline

: C27H41N2O2(1+)*I(1-)

Conditions

Conditions	Yield
Heating;

Ajmaline Specification

The Ajmaline, with the CAS registry number 4360-12-7, is also known as Ajmalan-17,21-diol, (17R,21alpha)-. It belongs to the product categories of Alkaloids; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 224-439-4. This chemical's molecular formula is C₂₀H₂₆N₂O₂ and molecular weight is 326.43. What's more, its systematic name is called (15α,17R,21α)-Ajmalan-17,21-diol. It should be stored in a sealed place. Ajmaline is an alkaloid that is class Ia antiarrhythmic agent. It is often used to bring out typical findings of ST elevations in patients suspected of having Brugada syndrome.

Physical properties about Ajmaline are: (1)ACD/LogP: 1.806; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.61; (4)ACD/LogD (pH 7.4): 1.10; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 2.75; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 45.24; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 46.94 Å²; (13)Index of Refraction: 1.701; (14)Molar Refractivity: 92.025 cm³; (15)Molar Volume: 237.825 cm³; (16)Polarizability: 36.482×10^-24cm³; (17)Surface Tension: 67.635 dyne/cm; (18)Density: 1.373 g/cm³; (19)Flash Point: 285.155 °C; (20)Enthalpy of Vaporization: 83.397 kJ/mol; (21)Boiling Point: 519.406 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is toxic if swallowed. It is harmful by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing and keep away from food, drink and animal feeding stuffs. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: CC[C@H]1[C@H]5C[C@@H]4N([C@@H]1O)[C@H]6C[C@]3(c2ccccc2N(C)[C@H]34)[C@H](O)C56
(2) InChI: InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11+,14-,15-,16?,17-,18+,19+,20+/m0/s1
(3) InChIKey: CJDRUOGAGYHKKD-SXKXKDIKSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	178mg/kg (178mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
child	LDLo	oral	53125ug/kg (53.125mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	Journal of Forensic Sciences. Vol. 33, Pg. 558, 1988.
guinea pig	LDLo	intravenous	28mg/kg (28mg/kg)	CARDIAC: CHANGE IN RATE	Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.
man	TDLo	oral	32mg/kg (32mg/kg)	CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: CYANOSIS	American Heart Journal. Vol. 70, Pg. 719, 1965.
mouse	LD50	intraperitoneal	75mg/kg (75mg/kg)		National Technical Information Service. Vol. AD691-490,
mouse	LD50	intravenous	21mg/kg (21mg/kg)		European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 188, 1975.
mouse	LD50	oral	255mg/kg (255mg/kg)	CARDIAC: CHANGE IN RATE	Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.
mouse	LD50	subcutaneous	180mg/kg (180mg/kg)	CARDIAC: CHANGE IN RATE	Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.
mouse	LD50	unreported	220mg/kg (220mg/kg)		Pharmaceutical Chemistry Journal Vol. 21, Pg. 331, 1987.
quail	LDLo	oral	316mg/kg (316mg/kg)		Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat	LD50	intraperitoneal	94mg/kg (94mg/kg)		Pharmaceutical Chemistry Journal Vol. 21, Pg. 331, 1987.
rat	LD50	intravenous	26mg/kg (26mg/kg)	CARDIAC: OTHER CHANGES	Pharmazie. Vol. 31, Pg. 36, 1976.
rat	LD50	oral	360mg/kg (360mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Pharmazie. Vol. 31, Pg. 39, 1976.
rat	LD50	subcutaneous	216mg/kg (216mg/kg)	CARDIAC: CHANGE IN RATE	Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.
women	LDLo	oral	50mg/kg (50mg/kg)		Journal of Forensic Sciences. Vol. 33, Pg. 558, 1988.

Product Name

Ajmaline

Synthetic route

Ajmaline Specification

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