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550-90-3

550-90-3 structure
550-90-3 structure
  • Name: 15-Oxosparteine
  • Chemical Name: lupanine
  • CAS Number: 550-90-3
  • Molecular Formula: C30H52
  • Molecular Weight: 412.734
  • Catalog: Natural product Alkaloid
  • Create Date: 2016-09-28 10:20:30
  • Modify Date: 2025-08-22 16:24:47
  • Lupanin (D-Lupanine) is a natural ketonic derivative of Sparteine ((+)-Sparteine (HY-W008350)) with a ganglioplegic activity. Lupanine shows binding affinity for nicotinic receptor (nAChR) with a Ki value of 500 nM[1].
Name lupanine
Synonyms 2-oxosparteine
(7a,7aa,14a,14ab)-Dodecahydro-7,14-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one
Lupane
3-Pyrrolidinecarboxylic acid,2-oxo
Spartein-15-one
2-OXO-3-PYRROLIDINECARBOXYLIC ACID
15-Oxosparteine
7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one, dodecahydro-, (7S,7aS,14S,14aR)-
2-OXO-PYRROLIDINE-3-CARBOXYLIC ACID
Description Lupanin (D-Lupanine) is a natural ketonic derivative of Sparteine ((+)-Sparteine (HY-W008350)) with a ganglioplegic activity. Lupanine shows binding affinity for nicotinic receptor (nAChR) with a Ki value of 500 nM[1].
Related Catalog
Target

Ki: 500 nM (Nicotinic receptor) and 11000 nM (Muscarinic receptor)[1]

In Vitro Lupanine 对烟碱受体具有结合亲和力，Ki 值为 500 nM。而 Lupanine 对毒蕈碱受体的亲和力非常弱，Ki 值为 11000 nM[1]。
In Vivo Lupanine (腹腔注射 100-300 毫克/千克；口服 175-700 毫克/千克) 在 EOPS 雄性瑞士小鼠 (20-22 克) 和哈特利豚鼠 (400-500 克) 中单次注射的毒性要小得多 [1]。 Lupanine (1-7.5 mg/kg；i.v.) 比 Sparteine 更有效地对抗颈动脉闭塞引起的继发性反射性高血压和刺激肺胃神经引起的猫狗低血压[1]。 Lupanine 对阿托品治疗的狗注射乙酰胆碱 (500 pg/kg i.v.) 引起的烟碱型高血压有抑制作用[1]。
References

[1]. K Yovo,, et al. Comparative pharmacological study of sparteine and its ketonic derivative lupanine from seeds of Lupinus albus. Planta Med. 1984 Oct;50(5):420-4.  

Density 0.9±0.1 g/cm3
Boiling Point 457.4±12.0 °C at 760 mmHg
Melting Point 40-44°
Molecular Formula C30H52
Molecular Weight 412.734
Flash Point 221.8±13.1 °C
Exact Mass 412.406891
PSA 23.55000
LogP 13.33
Vapour Pressure 0.0±0.5 mmHg at 25°C
Index of Refraction 1.498

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OK5745000
CHEMICAL NAME :
Lupanine
CAS REGISTRY NUMBER :
550-90-3
LAST UPDATED :
198806
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C15-H24-N2-O
MOLECULAR WEIGHT :
248.41
WISWESSER LINE NOTATION :
T C66 K66 A GVN PNTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1440 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 210,27,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
177 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis
REFERENCE :
JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 7,51,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
410 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
PLMEAA Planta Medica. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1953- Volume(issue)/page/year: 50,420,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
175 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
PLMEAA Planta Medica. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1953- Volume(issue)/page/year: 50,420,1984
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JAGRAC Journal of Agricultural Research (Washington, DC). (Washington, DC) V.1-78, 1913-49. Discontinued. Volume(issue)/page/year: 32,51,1926
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
78 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
PLMEAA Planta Medica. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1953- Volume(issue)/page/year: 50,420,1984
Hazard Codes Xi
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