(+)-Morphine

(+)-Morphine
Identifiers
	IUPAC name (4S,4aS,7R,7aS,12bR)-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol;
CAS Number	65165-99-3 ;
PubChem CID	5479215;
ChemSpider	4586177 ;
Chemical and physical data
Formula	C17H19NO3
Molar mass	285.343 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CC[C@@]23[C@H]4[C@@H]1CC5=C2C(=C(C=C5)O)O[C@@H]3[C@@H](C=C4)O;
	InChI InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m1/s1 ; Key:BQJCRHHNABKAKU-QHQPWPDESA-N ;

(+)-Morphine also known as dextro-morphine is the "unnatural" enantiomer of the opioid drug (−)-morphine. Unlike "natural" levo-morphine, unnatural dextro-morphine is not present in Papaver somniferum and is the product of laboratory synthesis.

In contrast to natural morphine, the unnatural enantiomer has no affinity or efficacy for the mu opioid receptor and therefore has no analgesic effects. To the contrary, in rats, (+)-morphine acts as an antianalgesic and is approximately 71,000 times more potent as an antianalgesic than (−)-morphine is as an analgesic.^[1] (+)-Morphine derives its antianalgesic effects by being a selective-agonist of the Toll-like receptor 4 (TLR4), which due to not binding to opioid receptors allows it to effectively reverse the analgesic properties of (−)-morphine. TLR4 is involved in immune system responses, and activation of TLR4 induces glial activation and release of inflammatory mediators such as TNF-α and Interleukin-1.^[2]^[3]

References

^ Wu HE, Thompson J, Sun HS, Terashvili M, Tseng LF (September 2005). "Antianalgesia: stereoselective action of dextro-morphine over levo-morphine on glia in the mouse spinal cord". The Journal of Pharmacology and Experimental Therapeutics. 314 (3): 1101–1108. doi:10.1124/jpet.105.087130. PMID 15901793. S2CID 7190985.
^ Hutchinson MR, Zhang Y, Shridhar M, Evans JH, Buchanan MM, Zhao TX, et al. (January 2010). "Evidence that opioids may have toll-like receptor 4 and MD-2 effects". Brain, Behavior, and Immunity. 24 (1): 83–95. doi:10.1016/j.bbi.2009.08.004. PMC 2788078. PMID 19679181.
^ Hutchinson MR, Lewis SS, Coats BD, Rezvani N, Zhang Y, Wieseler JL, et al. (May 2010). "Possible involvement of toll-like receptor 4/myeloid differentiation factor-2 activity of opioid inactive isomers causes spinal proinflammation and related behavioral consequences". Neuroscience. 167 (3): 880–893. doi:10.1016/j.neuroscience.2010.02.011. PMC 2854318. PMID 20178837.

[1] Wu HE, Thompson J, Sun HS, Terashvili M, Tseng LF (September 2005). "Antianalgesia: stereoselective action of dextro-morphine over levo-morphine on glia in the mouse spinal cord". The Journal of Pharmacology and Experimental Therapeutics. 314 (3): 1101–1108. doi:10.1124/jpet.105.087130. PMID 15901793. S2CID 7190985.

[2] Hutchinson MR, Zhang Y, Shridhar M, Evans JH, Buchanan MM, Zhao TX, et al. (January 2010). "Evidence that opioids may have toll-like receptor 4 and MD-2 effects". Brain, Behavior, and Immunity. 24 (1): 83–95. doi:10.1016/j.bbi.2009.08.004. PMC 2788078. PMID 19679181.

[3] Hutchinson MR, Lewis SS, Coats BD, Rezvani N, Zhang Y, Wieseler JL, et al. (May 2010). "Possible involvement of toll-like receptor 4/myeloid differentiation factor-2 activity of opioid inactive isomers causes spinal proinflammation and related behavioral consequences". Neuroscience. 167 (3): 880–893. doi:10.1016/j.neuroscience.2010.02.011. PMC 2854318. PMID 20178837.

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See also

References