IDPN (chemical)

IDPN
Names
	Preferred IUPAC name 3,3′-Azanediyldipropanenitrile
	Other names Bis(2-cyanoethyl)amine
Identifiers
CAS Number	111-94-4;
3D model (JSmol)	Interactive image;
ChemSpider	7857;
ECHA InfoCard	100.003.566
EC Number	203-922-3;
PubChem CID	8149;
UNII	3XP1CVU865;
UN number	3334
CompTox Dashboard (EPA)	DTXSID2041464 ;
	InChI InChI=1S/C6H9N3/c7-3-1-5-9-6-2-4-8/h9H,1-2,5-6H2 Key: SBAJRGRUGUQKAF-UHFFFAOYSA-N;
	SMILES C(CNCCC#N)C#N;
Properties
Chemical formula	C6H9N3
Molar mass	123.159 g·mol−1
Density	1.02
Melting point	−5.5 °C (22.1 °F; 267.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

IDPN (3,3'-iminodipropanenitrile) is a neurotoxin with ototoxic and hepatotoxic effects. It causes irreversible movement disorder.^[1]^[2]^[3]

Ototoxicity

IDPN has been shown to kill vestibular hair cells, disrupting normal vestibular function, in rats,^[4] mice, guinea pigs, and frogs.^[5] In rodents, the loss of vestibular function results in balance-related deficits, including circling behavior, retropulsion, and head bobbing, as well as weight loss.^[5] Type I hair cells are more sensitive to IDPN toxicity than Type II hair cells.^[4] No regeneration of vestibular hair cells was observed, thus these effects can be considered to be irreversible.^[4]

IDPN has also been shown to kill cochlear hair cells, affecting auditory function.^[6] IDPN-induced hearing loss covered a broad range of frequencies.

References

^ Sedó-Cabezón, Lara; Jedynak, Paulina; Boadas-Vaello, Pere; Llorens, Jordi (1 October 2015). "Transient alteration of the vestibular calyceal junction and synapse in response to chronic ototoxic insult in rats". Disease Models & Mechanisms. 8 (10): 1323–1337. doi:10.1242/dmm.021436. PMC 4610239. PMID 26398945.
^ Khan, HA; Ibrahim, KE (12 October 2015). "Pattern of neurobehavioral and organ-specific toxicities of β, β'-iminodipropionitrile in mice". Archives of Medical Science. 11 (5): 1137–44. doi:10.5114/aoms.2015.54871 (inactive 1 November 2024). PMC 4624758. PMID 26528360.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
^ Ogata, Keiko; Kushida, Masahiko; Miyata, Kaori; Sumida, Kayo; Takeda, Shuji; Izawa, Takeshi; Kuwamura, Mitsuru; Yamate, Jyoji (2016). "Alteration of microRNA expressions in the pons and medulla in rats after 3,3′-iminodipropionitrile administration". Journal of Toxicologic Pathology. 29 (4): 229–236. doi:10.1293/tox.2016-0019. PMC 5097965. PMID 27821907.
^ ^a ^b ^c Llorens, J.; Demêmes, D. (1994-06-01). "Hair cell degeneration resulting from 3,3'-iminodipropionitrile toxicity in the rat vestibular epithelia". Hearing Research. 76 (1–2): 78–86. doi:10.1016/0378-5955(94)90090-6. ISSN 0378-5955. PMID 7928719. S2CID 4761312.
^ ^a ^b Soler-Martín, Carla; Díez-Padrisa, Núria; Boadas-Vaello, Pere; Llorens, Jordi (2007-03-01). "Behavioral Disturbances and Hair Cell Loss in the Inner Ear Following Nitrile Exposure in Mice, Guinea Pigs, and Frogs". Toxicological Sciences. 96 (1): 123–132. doi:10.1093/toxsci/kfl186. ISSN 1096-6080. PMID 17159233.
^ Crofton, K. M.; Janssen, R.; Prazma, J.; Pulver, S.; Barone, S. (November 1994). "The ototoxicity of 3,3'-iminodipropionitrile: functional and morphological evidence of cochlear damage". Hearing Research. 80 (2): 129–140. doi:10.1016/0378-5955(94)90104-X. ISSN 0378-5955. PMID 7896571. S2CID 4699179.

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[1] Sedó-Cabezón, Lara; Jedynak, Paulina; Boadas-Vaello, Pere; Llorens, Jordi (1 October 2015). "Transient alteration of the vestibular calyceal junction and synapse in response to chronic ototoxic insult in rats". Disease Models & Mechanisms. 8 (10): 1323–1337. doi:10.1242/dmm.021436. PMC 4610239. PMID 26398945.

[2] Khan, HA; Ibrahim, KE (12 October 2015). "Pattern of neurobehavioral and organ-specific toxicities of β, β'-iminodipropionitrile in mice". Archives of Medical Science. 11 (5): 1137–44. doi:10.5114/aoms.2015.54871 (inactive 1 November 2024). PMC 4624758. PMID 26528360.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)

[3] Ogata, Keiko; Kushida, Masahiko; Miyata, Kaori; Sumida, Kayo; Takeda, Shuji; Izawa, Takeshi; Kuwamura, Mitsuru; Yamate, Jyoji (2016). "Alteration of microRNA expressions in the pons and medulla in rats after 3,3′-iminodipropionitrile administration". Journal of Toxicologic Pathology. 29 (4): 229–236. doi:10.1293/tox.2016-0019. PMC 5097965. PMID 27821907.

[Llorens_1994-4] Llorens, J.; Demêmes, D. (1994-06-01). "Hair cell degeneration resulting from 3,3'-iminodipropionitrile toxicity in the rat vestibular epithelia". Hearing Research. 76 (1–2): 78–86. doi:10.1016/0378-5955(94)90090-6. ISSN 0378-5955. PMID 7928719. S2CID 4761312.

[Soler-Martín_2007-5] Soler-Martín, Carla; Díez-Padrisa, Núria; Boadas-Vaello, Pere; Llorens, Jordi (2007-03-01). "Behavioral Disturbances and Hair Cell Loss in the Inner Ear Following Nitrile Exposure in Mice, Guinea Pigs, and Frogs". Toxicological Sciences. 96 (1): 123–132. doi:10.1093/toxsci/kfl186. ISSN 1096-6080. PMID 17159233.

[6] Crofton, K. M.; Janssen, R.; Prazma, J.; Pulver, S.; Barone, S. (November 1994). "The ototoxicity of 3,3'-iminodipropionitrile: functional and morphological evidence of cochlear damage". Hearing Research. 80 (2): 129–140. doi:10.1016/0378-5955(94)90104-X. ISSN 0378-5955. PMID 7896571. S2CID 4699179.

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