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MedKoo Cat#: 574350 | Name: Dimaprit HCl
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Description:

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

Dimaprit HCl is a histamine H2 receptor agonist selective for histamine H2 over H1 and H3 receptors. Dimaprit HCl inhibits histamine release from isolated peritoneal mast cells and stimulates gastric acid secretion in vivo. Dimaprit inhibits 2-(2-pyridyl)ethylamine-induced bronchoconstriction in a dose-dependent manner.

Chemical Structure

Dimaprit HCl
CAS#23256-33-9

Theoretical Analysis

MedKoo Cat#: 574350

Name: Dimaprit HCl

CAS#: 23256-33-9

Chemical Formula: C6H17Cl2N3S

Exact Mass: 0.0000

Molecular Weight: 234.18

Elemental Analysis: C, 30.77; H, 7.32; Cl, 30.28; N, 17.94; S, 13.69

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 550.00 2 Weeks
250mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Dimaprit HCl; Dimaprit 2HCl; Dimaprit hydrochloride; Dimaprit Dihydrochloride
IUPAC/Chemical Name
carbamimidothioic acid, 3-(dimethylamino)propyl ester, dihydrochloride
InChi Key
DFWCPLGXFMSUCW-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H15N3S.2ClH/c1-9(2)4-3-5-10-6(7)8;;/h3-5H2,1-2H3,(H3,7,8);2*1H
SMILES Code
NC(SCCCN(C)C)=N.Cl.Cl
Appearance
Solid powder
Purity
>95% (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
Shelf Life
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Dimaprit dihydrochloride is a selective histamine H2 receptor agonist, it also inhibits nNOS with an IC50 of 49 μM.
In vitro activity:
Treatment with dimaprit at 6 and 60 microM for 20 min significantly inhibited the anaphylactic histamine release, whereas betahistine at up to 80 microM under the same conditions did not affect it. Treatment with dimaprit at 6 and 60 microM for 1 to 20 min and for 5 to 20 min, respectively, caused a time-dependent inhibition of the release, but up to 30 min treatment with 8 and 80 microM betahistine had no effect. Reference: Jpn J Pharmacol. 1993 May;62(1):75-9. https://pubmed.ncbi.nlm.nih.gov/7688057/
In vivo activity:
Dimaprit and some of its analogues were tested in an in vitro assay which measures the conversion of [3H]-L-arginine to [3H]-L-citrulline. Dimaprit inhibits rat brain NOS (nNOS) concentration dependently with an IC50 of 49+/-14 microM. Reference: Br J Pharmacol. 1999 May;127(2):331-4. https://pubmed.ncbi.nlm.nih.gov/10385230/
Solvent mg/mL mM comments
Solubility
DMSO 30.0 128.10
DMSO:PBS (pH 7.2) (1:3) 0.3 1.07
Water 23.4 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 234.18 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Kohno S, Ogawa K, Nabe T, Yamamura H, Ohata K. Dimaprit, a histamine H2-agonist, inhibits anaphylactic histamine release from mast cells and the decreased release is restored by thioperamide (H3-antagonist), but not by cimetidine (H2-antagonist). Jpn J Pharmacol. 1993 May;62(1):75-9. doi: 10.1254/jjp.62.75. PMID: 7688057. 2. Motoki A, Adachi N, Liu K, Takahashi HK, Nishibori M, Yorozuya T, Arai T, Nagaro T. Suppression of ischaemia-induced cytokine release by dimaprit and amelioration of liver injury in rats. Basic Clin Pharmacol Toxicol. 2008 Apr;102(4):394-8. doi: 10.1111/j.1742-7843.2008.00219.x. Epub 2008 Feb 29. PMID: 18312491. 3. Paquay JB, Hoen PA, Voss HP, Bast A, Timmerman H, Haenen GR. Nitric oxide synthase inhibition by dimaprit and dimaprit analogues. Br J Pharmacol. 1999 May;127(2):331-4. doi: 10.1038/sj.bjp.0702552. PMID: 10385230; PMCID: PMC1566025.
In vitro protocol:
1. Kohno S, Ogawa K, Nabe T, Yamamura H, Ohata K. Dimaprit, a histamine H2-agonist, inhibits anaphylactic histamine release from mast cells and the decreased release is restored by thioperamide (H3-antagonist), but not by cimetidine (H2-antagonist). Jpn J Pharmacol. 1993 May;62(1):75-9. doi: 10.1254/jjp.62.75. PMID: 7688057.
In vivo protocol:
1. Motoki A, Adachi N, Liu K, Takahashi HK, Nishibori M, Yorozuya T, Arai T, Nagaro T. Suppression of ischaemia-induced cytokine release by dimaprit and amelioration of liver injury in rats. Basic Clin Pharmacol Toxicol. 2008 Apr;102(4):394-8. doi: 10.1111/j.1742-7843.2008.00219.x. Epub 2008 Feb 29. PMID: 18312491. 2. Paquay JB, Hoen PA, Voss HP, Bast A, Timmerman H, Haenen GR. Nitric oxide synthase inhibition by dimaprit and dimaprit analogues. Br J Pharmacol. 1999 May;127(2):331-4. doi: 10.1038/sj.bjp.0702552. PMID: 10385230; PMCID: PMC1566025.
1: Zhou J, Zaiss M, Knutsson L, Sun PZ, Ahn SS, Aime S, Bachert P, Blakeley JO, Cai K, Chappell MA, Chen M, Gochberg DF, Goerke S, Heo HY, Jiang S, Jin T, Kim SG, Laterra J, Paech D, Pagel MD, Park JE, Reddy R, Sakata A, Sartoretti-Schefer S, Sherry AD, Smith SA, Stanisz GJ, Sundgren PC, Togao O, Vandsburger M, Wen Z, Wu Y, Zhang Y, Zhu W, Zu Z, van Zijl PCM. Review and consensus recommendations on clinical APT-weighted imaging approaches at 3T: Application to brain tumors. Magn Reson Med. 2022 Aug;88(2):546-574. doi: 10.1002/mrm.29241. Epub 2022 Apr 22. PMID: 35452155; PMCID: PMC9321891. 2: Swaab RL, Battles AM, Bruner CA, Hough LB. Dimaprit--induced neurotoxicity. Agents Actions. 1992 Mar;35(3-4):179-84. doi: 10.1007/BF01997497. PMID: 1388319. 3: Smits PC, Frigoli E, Vranckx P, Ozaki Y, Morice MC, Chevalier B, Onuma Y, Windecker S, Tonino PAL, Roffi M, Lesiak M, Mahfoud F, Bartunek J, Hildick-Smith D, Colombo A, Stankovic G, Iñiguez A, Schultz C, Kornowski R, Ong PJL, Alasnag M, Rodriguez AE, Paradies V, Kala P, Kedev S, Al Mafragi A, Dewilde W, Heg D, Valgimigli M; MASTER DAPT Investigators. Abbreviated Antiplatelet Therapy After Coronary Stenting in Patients With Myocardial Infarction at High Bleeding Risk. J Am Coll Cardiol. 2022 Sep 27;80(13):1220-1237. doi: 10.1016/j.jacc.2022.07.016. PMID: 36137672. 4: Durant GJ, Ganellin CR, Parsons ME. Dimaprit, (S-[3-(N,N-dimethylamino)propyl]isothiourea). A highly specific histamine H2-receptor agonist. Part 2. Structure-activity considerations. Agents Actions. 1977 Mar;7(1):39-43. doi: 10.1007/BF01964879. PMID: 860674. 5: Paquay JB, Hoen PA, Voss HP, Bast A, Timmerman H, Haenen GR. Nitric oxide synthase inhibition by dimaprit and dimaprit analogues. Br J Pharmacol. 1999 May;127(2):331-4. doi: 10.1038/sj.bjp.0702552. PMID: 10385230; PMCID: PMC1566025. 6: Durant GJ, Ganellin CR, Parsons ME. Dimaprit, [S-[3-(N,N-dimethylamino)propyl]isothiourea]. A highly specific histamine H2-receptor agonist. Part 2. Structure-activity considerations. 1977. Agents Actions. 1994 Dec;43(3-4):139-43. doi: 10.1007/BF01986680. PMID: 7725965. 7: Kohno S, Ogawa K, Nabe T, Yamamura H, Ohata K. Dimaprit, a histamine H2-agonist, inhibits anaphylactic histamine release from mast cells and the decreased release is restored by thioperamide (H3-antagonist), but not by cimetidine (H2-antagonist). Jpn J Pharmacol. 1993 May;62(1):75-9. doi: 10.1254/jjp.62.75. PMID: 7688057. 8: Taibl KR, Schantz S, Aung MT, Padula A, Geiger S, Smith S, Park JS, Milne GL, Robinson JF, Woodruff TJ, Morello-Frosch R, Eick SM. Associations of per- and polyfluoroalkyl substances (PFAS) and their mixture with oxidative stress biomarkers during pregnancy. Environ Int. 2022 Nov;169:107541. doi: 10.1016/j.envint.2022.107541. Epub 2022 Sep 27. PMID: 36191484; PMCID: PMC9846434. 9: Morini G, Coruzzi G, Bertaccini G. Contractile and relaxant effects of dimaprit on guinea pig isolated intestinal cells. Life Sci. 1997;60(25):PL377-82. doi: 10.1016/s0024-3205(97)00293-2. PMID: 9194693. 10: Flynn SB, Johnston BM, Owen DA. The cardiovascular response to dimaprit, a selective histamine H2-receptor agonist. Br J Pharmacol. 1977 Sep;61(1):101-7. PMID: 912163; PMCID: PMC1667663. 11: Motoki A, Adachi N, Liu K, Takahashi HK, Nishibori M, Yorozuya T, Arai T, Nagaro T. Suppression of ischaemia-induced cytokine release by dimaprit and amelioration of liver injury in rats. Basic Clin Pharmacol Toxicol. 2008 Apr;102(4):394-8. doi: 10.1111/j.1742-7843.2008.00219.x. Epub 2008 Feb 29. PMID: 18312491. 12: Soliman A, Cankara FN, Kortholt A. Allosteric inhibition of LRRK2, where are we now. Biochem Soc Trans. 2020 Oct 30;48(5):2185-2194. doi: 10.1042/BST20200424. PMID: 33079169; PMCID: PMC7609032. 13: Puebla L, Arilla E. Effect of dimaprit and cimetidine on the somatostatinergic system in the rat frontoparietal cortex. Neuropsychopharmacology. 1996 May;14(5):367-74. doi: 10.1016/0893-133X(95)00149-8. PMID: 8703305. 14: Fechner GA, Jacobs JJ, Parsons PG. Dimaprit analogues inhibit tyrosinase via a disulphide breakdown product independently of the histamine H2 receptor. Biochem Biophys Res Commun. 1994 Jun 15;201(2):687-93. doi: 10.1006/bbrc.1994.1755. PMID: 8003003. 15: Parsons ME, Owen DA, Ganellin CR, Durant GJ. Dimaprit -(S-[3-(N,N-dimethylamino)prophyl]isothiourea) - a highly specific histamine H2 -receptor agonist. Part 1. Pharmacology. Agents Actions. 1977 Mar;7(1):31-7. doi: 10.1007/BF01964878. PMID: 871093. 16: Leitfaden der APT „Exposition von Betreuungs- und Begleitpersonen“. Rofo. 2021 Aug;193(8):975. German. doi: 10.1055/a-1542-2204. Epub 2021 Jul 20. PMID: 34284517. 17: Pelc LR, Christensen CW, Gross GJ, Warltier DC. Direct cardiac actions of the H2 receptor agonists, impromidine and dimaprit. Eur J Pharmacol. 1985 Jan 8;107(3):379-84. doi: 10.1016/0014-2999(85)90266-3. PMID: 3156752. 18: Luo Y, Zhang GQ, Li ZY. Reply to Dr. Yarandi. Pediatr Allergy Immunol. 2019 Jun;30(4):495-496. doi: 10.1111/pai.13053. Epub 2019 May 20. PMID: 30916424. 19: van Zijl PCM. APT-weighted MRI Can Be an Early Marker for Demyelination. Radiology. 2021 May;299(2):435-437. doi: 10.1148/radiol.2021210041. Epub 2021 Mar 16. PMID: 33729012. 20: Kalinyak KA, Sawutz DG, Lampkin BC, Johnson CL, Whitsett JA. Effects of dimaprit on growth and differentiation of human promyelocytic cell line, HL-60. Life Sci. 1985 May 20;36(20):1909-16. doi: 10.1016/0024-3205(85)90439-4. PMID: 2985904.