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Dipropyldopamine

From Wikipedia, the free encyclopedia
Pharmaceutical compound
Dipropyldopamine
Clinical data
Other namesDPDA;N,N-Di-n-propyldopamine;N,N-Dipropyldopamine;N,N-Di-n-propyl-DA;N,N-Dipropyl-DA
Drug classDopamine receptor agonist;DopamineD1 andD2-like receptoragonist
ATC code
  • None
Identifiers
  • 4-[2-(dipropylamino)ethyl]benzene-1,2-diol
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC14H23NO2
Molar mass237.343 g·mol−1
3D model (JSmol)
  • CCCN(CCC)CCC1=CC(=C(C=C1)O)O
  • InChI=1S/C14H23NO2/c1-3-8-15(9-4-2)10-7-12-5-6-13(16)14(17)11-12/h5-6,11,16-17H,3-4,7-10H2,1-2H3
  • Key:LMYSNFBROWBKMB-UHFFFAOYSA-N

Dipropyldopamine (DPDA), also known asN,N-di-n-propyldopamine, is asyntheticdopamine receptor agonist related to thecatecholamineneurotransmitterdopamine which has been used inscientific research.[1][2] It is a dualagonist of both dopamineD1-like andD2-like receptors, with much greaterpotency at dopamineD2 receptors than dopamine itself.[2][3] Unlike dopamine, the drug lacksβ-adrenergic receptor activity and also has weakervasoconstrictor effects.[1]

DPDA produceshypolocomotion across a wide range of doses in rodents.[4][5] It modestly reduces climbing behavior at low doses and markedly enhances it at much high doses.[6] The drug is thought to be resistant tometabolism bymonoamine oxidase (MAO) but to still be susceptible to metabolism bycatecholO-methyltransferase (COMT).[7] It was virtually inactiveorally in rodents.[8] In contrast to dopamine, which isperipherally selective, DPDA can cross theblood–brain barrier and produce effects in thecentral nervous system.[8]

DPDA was first described in thescientific literature by 1977.[9] OtherN,N-dialkylderivatives of dopamine besides DPDA have been studied.[4] In addition,esters of DPDA have been developed and studied.[8]

See also

[edit]

References

[edit]
  1. ^abKohli JD, Goldberg LI, Volkman PH, Cannon JG (October 1978). "N,N-Di-n-propyl dopamine: a qualitatively different dopamine vascular agonist".J Pharmacol Exp Ther.207 (1):16–22.doi:10.1016/S0022-3565(25)31387-X.PMID 702336.
  2. ^abKohli JD (June 1990). "Peripheral dopamine receptors".Am J Hypertens.3 (6 Pt 2):25S–28S.doi:10.1093/ajh/3.6.25s.PMID 2143385.
  3. ^Mailman, Richard B.; Nichols, David E.; Tropsha, Alexander (1997)."Molecular Drug Design and Dopamine Receptors".The Dopamine Receptors. Totowa, NJ: Humana Press. pp. 105–133.doi:10.1007/978-1-4757-2635-0_4.ISBN 978-1-4757-2637-4. Retrieved9 February 2026.
  4. ^abCostall B, Lim SK, Naylor RJ (July 1981). "Characterisation of the mechanisms by which purported dopamine agonists reduce spontaneous locomotor activity of mice".Eur J Pharmacol.73 (2–3):175–188.doi:10.1016/0014-2999(81)90089-3.PMID 6118281.
  5. ^Bradbury, A.J.; Costall, B.; Lim, S.K.; Naylor, R.J. (1982). "Reduction in Spontaneous Locomotor Activity by Purported Dopamine Agonists: an Analysis of the Site and Mechanism of Action".Advances in Dopamine Research. Elsevier. pp. 413–424.doi:10.1016/b978-0-08-027391-4.50046-0.ISBN 978-0-08-027391-4. Retrieved9 February 2026.
  6. ^Costall B, Eniojukan JF, Naylor RJ (November 1982). "Spontaneous climbing behaviour of mice, its measurement and dopaminergic involvement".Eur J Pharmacol.85 (2):125–132.doi:10.1016/0014-2999(82)90457-5.PMID 7151866.
  7. ^Sumners C, Dijkstra D, de Vries JB, Horn AS (July 1981). "Neurochemical and behavioural profiles of five dopamine analogues".Naunyn Schmiedebergs Arch Pharmacol.316 (4):304–310.doi:10.1007/BF00501362.PMID 7196506.
  8. ^abcWikström H, Lindberg P, Martinson P, Hjorth S, Carlsson A (September 1978). "Pivaloyl esters of N,N-dialkylated dopamine congeners. Central dopamine-receptor stimulating activity".J Med Chem.21 (9):864–867.doi:10.1021/jm00207a005.PMID 722753.
  9. ^Volkman, P. H., Kohli, J. D., Goldberg, L. I., & Cannon, J. G. (1977, January). Dipropyldopamine, a qualitatively different dopamine (DA) agonist. In Federation Proceedings (Vol. 36, No. 3, pp. 1049–1049).https://scholar.google.com/scholar?cluster=12367958232674843975
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