Synonym
Alphaprodine Hydrochloride; Nisentil; Nisintel; Prisilidene hydrochloride; Nisentil hydrochloride; Alpha-Prodine hydrochloride;
IUPAC/Chemical Name
[(3S,4R)-1,3-dimethyl-4-phenylpiperidin-4-yl] propanoate;hydrochloride
InChi Key
LFLUADVCIBEPQJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H23NO2.ClH/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2;/h5-9,13H,4,10-12H2,1-3H3;1H
SMILES Code
CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2.Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
297.82
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Lagarde LA, Ortiz de la Peña R, Bravo Serradell O. [Three auxiliary medications in obstetrics. 1955]. Ginecol Obstet Mex. 2010 Nov;78(11):633-41. Spanish. PubMed PMID: 21299003.
2: Fredenhagen A, Molleyres LP, Böhlendorf B, Laue G. Structure determination of neoefrapeptins A to N: peptides with insecticidal activity produced by the fungus Geotrichum candidum. J Antibiot (Tokyo). 2006 May;59(5):267-80. PubMed PMID: 16883776.
3: Yin D, Khanolkar AD, Makriyannis A, Froimowitz M. Chiral resolution of 1,3-dimethyl-4-phenylpiperidine derivatives using high-performance liquid chromatography with a chiral stationary phase. J Chromatogr A. 1994 Aug 26;678(1):176-9. PubMed PMID: 7921191.
4: Wünsch B, Höfner G, Bauschke G. [Synthesis and CNS-activity of spirocyclic pethidine and prodine analogs]. Arch Pharm (Weinheim). 1993 Sep;326(9):513-8. German. PubMed PMID: 8239944.
5: Adams RJ. Obstetrical medication and the newborn infant. II: The influence of meperidine (pethidine) on visual behaviour. Dev Med Child Neurol. 1992 Mar;34(3):247-51. PubMed PMID: 1559604.
6: Egley CC, Bowes WA Jr, Wagner D. Sinusoidal fetal heart rate pattern during labor. Am J Perinatol. 1991 May;8(3):197-202. PubMed PMID: 2029281.
7: Iorio MA, Frigeni V, Bowman ER, Harris LS, May EL, Aceto MD. Common stereospecificity of opioid and dopamine systems for N-butyrophenone prodine-like compounds. J Med Chem. 1991 Jan;34(1):194-7. PubMed PMID: 1671414.
8: Wynn RL, Bergman SA, Rudo FG, Leventer M. GABAmimetics diminish antinociception of meperidine under conditions which enhance other opioid mu-agonists. Arch Int Pharmacodyn Ther. 1990 Mar-Apr;304:136-46. PubMed PMID: 2173504.
9: Adams RJ. Obstetrical medication and the human newborn: the influence of alphaprodine hydrochloride on visual behaviour. Dev Med Child Neurol. 1989 Oct;31(5):650-6. PubMed PMID: 2806744.
10: Matthews MK. The relationship between maternal labour analgesia and delay in the initiation of breastfeeding in healthy neonates in the early neonatal period. Midwifery. 1989 Mar;5(1):3-10. PubMed PMID: 2927331.
11: Lunt RC, Hward HE. A descriptive study of 201 uncombined alphaprodine HCl conscious sedations in pediatric dental patients (1982-1985). Pediatr Dent. 1988 Jun;10(2):121-6. PubMed PMID: 3269520.
12: Kuhnert BR, Brashear WT, Syracuse CD. Measurement of alphaprodine by selected-ion monitoring. J Chromatogr. 1988 Apr 29;426(2):392-8. PubMed PMID: 3392151.
13: Lambert LA, Nazif MM, Moore PA, Zullo TG. Nonlinear dose-response characteristics of alphaprodine sedation in preschool children. Pediatr Dent. 1988 Mar;10(1):30-3. PubMed PMID: 3268795.
14: Moore PA. Local anesthesia and narcotic drug interaction in pediatric dentistry. Anesth Prog. 1988 Jan-Feb;35(1):17. PubMed PMID: 3422794; PubMed Central PMCID: PMC2190049.
15: Bevacqua BK. Supraventricular tachycardia associated with postpartum metoclopramide administration. Anesthesiology. 1988 Jan;68(1):124-5. PubMed PMID: 3337365.
16: Currie WR, Biery KA, Campbell RL, Mourino AP. Narcotic sedation: an evaluation of cardiopulmonary parameters and behavior modification in pediatric dental patients. J Pedod. 1988 Spring;12(3):230-49. PubMed PMID: 3268655.
17: Shane SM, Speedie LJ, Rao L, Niedermeyer E, McPherson R. Conscious sedation for minor gynecologic surgery in the ambulatory patient. A pilot study. Anesth Prog. 1987 Nov-Dec;34(6):211-4. PubMed PMID: 3481518; PubMed Central PMCID: PMC2190040.
18: Speedie LJ, Tung TJ, Shane SM, Chase GA, Brake N, Epstein MH. Comparison of two intravenous sedation techniques for percutaneous radio frequency trigeminal rhizotomy. A pilot study. Anesth Prog. 1987 Nov-Dec;34(6):207-10. PubMed PMID: 3481517; PubMed Central PMCID: PMC2190044.
19: Iorio MA, Reymer TP, Frigeni V. Combined analgesic/neuroleptic activity in N-butyrophenone prodine-like compounds. J Med Chem. 1987 Oct;30(10):1906-10. PubMed PMID: 2888899.
20: Gross R, Nazif MM, Zullo T. Effects of variable alphaprodine dose levels on arterial blood gases in rhesus monkeys. Anesth Prog. 1987 Mar-Apr;34(2):43-5. PubMed PMID: 3111312; PubMed Central PMCID: PMC2148565.
