Levallorphan | CAS#152-02-3 | KOR agonist

MedKoo Cat#: 318092 | Name: Levallorphan

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levallorphan, also known as levallorphan tartate (USAN), is an opioid modulator of the morphinan family used as an opioid analgesic and opioid antagonist/antidote. It acts as an antagonist of the μ-opioid receptor (MOR) and as an agonist of the κ-opioid receptor (KOR), and as a result, blocks the effects of stronger agents with greater intrinsic activity such as morphine whilst simultaneously producing analgesia. As an agonist of the KOR, levallorphan can produce severe mental reactions at sufficient doses including hallucinations, dissociation, and other psychotomimetic effects, dysphoria, anxiety, confusion, dizziness, disorientation, derealization, feelings of drunkenness, and bizarre, unusual, or disturbing dreams. (Source: https://en.wikipedia.org/wiki/Levallorphan).

Chemical Structure

Levallorphan

CAS#152-02-3

Theoretical Analysis

MedKoo Cat#: 318092

Name: Levallorphan

CAS#: 152-02-3

Chemical Formula: C19H25NO

Exact Mass: 283.1936

Molecular Weight: 283.41

Elemental Analysis: C, 80.52; H, 8.89; N, 4.94; O, 5.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Levallorphan; Naloxiphan; Lorfan; Levallorphane; Levallorphanum; Levalorfano; levallorphan tartate

IUPAC/Chemical Name

(−)-17-allylmorphinan-3-ol

InChi Key

OZYUPQUCAUTOBP-QXAKKESOSA-N

InChi Code

InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1

SMILES Code

C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O

Appearance

Solid powder

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 283.41 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: Bonn B, Masimirembwa CM, Castagnoli N Jr. Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan. Drug Metab Dispos. 2010 Jan;38(1):187-99. doi: 10.1124/dmd.109.028670. Epub . PubMed PMID: 19797609. 2: Okamoto Y, Suzuki T, Murayama S. Effects of naloxone and levallorphan on the spinal cord reflex potentials under the spinal ischemic condition in cats. Jpn J Pharmacol. 1992 Aug;59(4):435-41. PubMed PMID: 1434139. 3: Handa N, Matsumoto M, Kitagawa K, Uehara A, Ogawa S, Etani H, Yoneda S, Kimura K, Kamada T. Levallorphan and dynorphin improve motor dysfunction in Mongolian gerbils with unilateral carotid occlusion: the first application of the inclined plane method in the experimental cerebral ischemia. Life Sci. 1988;42(19):1825-31. PubMed PMID: 2897055. 4: Bianchi G, Fiocchi R, Peracchia F, Petrillo P, Tavani A, Manara L. The peripheral narcotic antagonist N-allyl levallorphan-bromide (CM 32191) selectively prevents morphine antipropulsive action and buprenorphine in-vivo binding in the rat intestine. J Pharm Pharmacol. 1984 May;36(5):326-30. PubMed PMID: 6145770. 5: Dragonetti M, Bianchetti A, Sacilotto R, Giudice A, Ferrarese N, Cattaneo C, Manara L. Levallorphan methyl iodide (SR 58002), a potent narcotic antagonist with peripheral selectivity superior to that of other quaternary compounds. Life Sci. 1983;33 Suppl 1:477-80. PubMed PMID: 6664228. 6: Tagashira E, Izumi T, Yanaura S. Mode of antagonistic action of levallorphan in morphine-dependent rats and assessment of physical dependence liability. Jpn J Pharmacol. 1979 Aug;29(4):623-30. PubMed PMID: 575396. 7: Yamamoto M, Kumagai F, Tachikawa S, Maeno H. Lack of effect of levallorphan on analgesia induced by intraventricular application of porcine calcitonin in mice. Eur J Pharmacol. 1979 Apr 15;55(2):211-3. PubMed PMID: 456419. 8: Lal S, Nair NP, Cervantes P, Pulman J, Guyda H. Effect of naloxone or levallorphan on serum prolactin concentrations and apomorphine-induced growth hormone secretion. Acta Psychiatr Scand. 1979 Feb;59(2):173-9. PubMed PMID: 420037. 9: Frelat G, Boquet PL. Levallorphan-tolerant mutants of Excherichia coli with altered morphologies. J Bacteriol. 1979 Feb;137(2):1013-6. PubMed PMID: 370088; PubMed Central PMCID: PMC218387. 10: Dame JB, Shapiro BM. Use of polymyxin B, levallorphan, and tetracaine to isolate novel envelope mutants of Escherichia coli. J Bacteriol. 1976 Aug;127(2):961-72. PubMed PMID: 182670; PubMed Central PMCID: PMC233006.