AJ-76 hydrochloride ((+)-AJ 76 hydrochloride) is a dopamine autoreceptor antagonist with pKi values of 6.95, 6.67, 6.37, 6.21 and 6.07 for hD3, hD4, hD2S, hD2 and rD2 receptors, respectively.

Physicochemical Properties

Molecular Formula	C15H24CLNO
Molecular Weight	269.81
Exact Mass	269.155
CAS #	85378-82-1
Related CAS #	85379-09-5
PubChem CID	13755572
Appearance	Typically exists as White to off-white solid at room temperature
LogP	4.306
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Heavy Atom Count	18
Complexity	231
Defined Atom Stereocenter Count	2
SMILES	CCCN[C@@H]1CCC2=C([C@@H]1C)C=CC=C2OC.Cl
InChi Key	KIRYNZFMOLYYQB-YECZQDJWSA-N
InChi Code	InChI=1S/C15H23NO.ClH/c1-4-10-16-14-9-8-13-12(11(14)2)6-5-7-15(13)17-3;/h5-7,11,14,16H,4,8-10H2,1-3H3;1H/t11-,14+;/m0./s1
Chemical Name	(1S,2R)-5-methoxy-1-methyl-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride
Synonyms	(+)-AJ 76 hydrochloride; 85378-82-1; (+)-AJ76Hydrochloride; (1S,2R)-5-methoxy-1-methyl-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride; (1S,2R)-5-methoxy-1-methyl-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride; (1S,2R)-5-methoxy-1-methyl-2-(propylamino)tetralin hydrochloride; cis-(+)-5-methoxy-1-methyl-2-(propylamino)tetralin hydrochloride; (1S,2R)-5-methoxy-1-methyl-N-propyl-1,2,3,4-tetrahydronaphthalen-2-aminium chloride;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Dopamine autoreceptor
ln Vivo	The biochemical and behavioral effects of the putative dopamine autoreceptor antagonists cis-(+)-5-methoxy-1-methyl-2-(n-propylamino)tetralin, (+)-AJ 76 and cis-(+)-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin, (+)-UH 232, were evaluated in various in vivo models in rats. Both compounds produced a marked elevation in brain dopamine synthesis and turnover with only slight effects on the synthesis and turnover of serotonin (5-HT) and noradrenaline being noted. (+)-AJ 76 and (+)-UH 232 also failed to antagonize the decrease in cortical noradrenaline synthesis rate caused by the alpha 2 agonist clonidine. The apomorphine-induced decrease in dopamine synthesis rate in gamma-butyrolactone (GBL) treated animals was completely blocked by (+)-AJ 76 and (+)-UH 232 but not by d-amphetamine or methylphenidate. In activity experiments using habituated animals, (+)-AJ 76 and (+)-UH 232 produced locomotor stimulation and weak stereotypies and antagonized the sedative effects of low doses of apomorphine. Locomotor hyperactivity induced by apomorphine or the dopamine agonist DiPr-5,6-ADTN was antagonized by (+)-UH 232 and to a lesser degree by (+)-AJ 76. The locomotor hyperactivity produced by (+)-AJ 76, (+)-UH 232 and methylphenidate was completely prevented by reserpine pretreatment and partially blocked by the tyrosine hydroxylase inhibitor alpha-methyl-para-tyrosine (alpha-MT), whereas d-amphetamine-induced hyperactivity was only antagonized by alpha-MT pretreatment. It is concluded that (+)-AJ 76 and (+)-UH 232 produce behavioral stimulation via a preferential antagonism on central dopamine autoreceptors, an action different from that of all known stimulants including apomorphine, d-amphetamine and methylphenidate. (+)-AJ 76 and (+)-UH 232 possess but weak antagonistic effects on postsynaptic dopamine receptors and only the latter compound is able to induce sedation in rats [1].
References	[1].Effects of repeated administration of the preferential dopamine autoreceptor antagonist, (+)-AJ76, on locomotor activity and brain DA metabolism in the rat. Eur J Pharmacol. 1991 Dec 3;205(3):241-6.
Additional Infomation	(1S,2R)-5-methoxy-1-methyl-2-(propylamino)tetralin hydrochloride is a hydrochloride obtained by reaction of (1S,2R)-5-methoxy-1-methyl-2-(propylamino)tetralin with one equivalent of hydrochloric acid. Dopamine receptor antagonist with preferential action at presynaptic receptors (pKi values are 6.95, 6.67, 6.37, 6.21 and 6.07 at hD3. hD4, hD2S, hD2L and rD2 receptors respectively). It has a role as a dopaminergic antagonist. It contains a (1S,2R)-5-methoxy-1-methyl-2-(propylammonio)tetralin(1+).

Solubility Data

Solubility (In Vitro)

Methanol :~25 mg/mL (~92.66 mM; with sonication) DMSO :~12.5 mg/mL (~46.33 mM; with sonication (<60°C))

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 1 mg/mL (3.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one),clear solution. For example, if 1 mL of working solution is to be prepared,you can add 100 μL of 10.0 mg/mL clear DMSO stock solution and add it to 900 μL of 20% SBE-β-CD in saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 1 mg/mL (3.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one),clear solution. For example, if 1 mL of working solution is to be prepared,you can add 100 μL of 10.0 mg/mL clear DMSO stock solution and add it to 900 μL corn oil and mix well.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.7063 mL	18.5316 mL	37.0631 mL
	5 mM	0.7413 mL	3.7063 mL	7.4126 mL
	10 mM	0.3706 mL	1.8532 mL	3.7063 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.